Material for organic electroluminescent device and organic electroluminescent device including the same

ABSTRACT

A material for an organic electroluminescent device having high emission efficiency and long life and an organic electroluminescent device including the same. The material for an organic electroluminescent device is represented by the following Formula 5.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims priority to and the benefit of JapanesePatent Application Nos. 2014-219497, filed on Oct. 28, 2014, and2015-092410, filed on Apr. 28, 2015, the entire contents of both areincorporated herein by reference.

BACKGROUND

The present disclosure herein relates to a material for an organicelectroluminescent device and an organic electroluminescent deviceincluding the same. For example, the present disclosure herein relatesto a material for an organic electroluminescent device having highemission efficiency and long life, and an organic electroluminescentdevice including the same.

Recently, the developments of organic electroluminescent (EL) displaysas one type of image displays are being actively conducted. Organic ELdevices are so-called self luminescent displays and are different fromliquid crystal displays. The organic EL devices display images byemitting light from a luminescent material (including an organicmaterial) in its emission layer via recombination of holes and electronsinjected from an anode and a cathode in the emission layer.

As an organic EL device, an organic device may include, for example, ananode, a hole transport layer disposed on the anode, an emission layerdisposed on the hole transport layer, an electron transport layerdisposed on the emission layer and a cathode disposed on the electrontransport layer. Holes are injected from the anode, and the injectedholes move via the hole transport layer and are injected into theemission layer. Electrons are injected from the cathode, and theinjected electrons move via the electron transport layer and areinjected into the emission layer. The injected holes and electronsrecombine to generate excitons in the emission layer. The organic ELdevice emits light utilizing light generated by the radiationdeactivation of the excitons. The configuration of the organic EL deviceis not limited thereto, however, and various modifications may bepossible.

When organic EL devices are applied to display apparatuses, the highefficiency and long life of the organic EL devices are required.However, in an organic EL device—particularly in a blue emission regionwhen compared to a green emission region and a red emission region, thedriving voltage is high and the emission efficiency is insufficient. Torealize the high efficiency and long life of an organic EL device, waysof increasing the normalization, stabilization and durability of thehole transport layer have been examined.

As a hole transport material utilized in a hole transport layer, variouscompounds such as an aromatic amine compound have been utilized.However, issues related to resolving the short life of the deviceremain. As a useful material for increasing the life of the organic ELdevice, for example, an amine derivative substituted with an aryl groupor a heteroaryl group has been suggested. However, an organic EL deviceutilizing the above-mentioned material has insufficient emission life.Thus, an organic EL device having higher efficiency and long emissionlife is desired at present.

SUMMARY

According to an embodiment of the disclosure, a material for an organicEL device is represented by Formula 1.

In Formula 1, X₁ is O or S; Ar₁ and Ar₂ are each independently asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms forforming a ring, a silyl group, a halogen atom, a deuterium atom, ahydrogen atom, or a substituted or unsubstituted dibenzoheterole grouphaving 10 to 30 carbon atoms for forming a ring and including an oxygenatom or a sulfur atom; Ar₃ and Ar₄ are each independently a silyl group,or a substituted or unsubstituted aryl group having 6 to 30 carbon atomsfor forming a ring; L₁ and L₂ are each independently a direct linkage,or a divalent group selected from a silyl group and a substituted orunsubstituted arylene group having 6 to 30 carbon atoms for forming aring; L₃ is a divalent group selected from a silyl group and asubstituted or unsubstituted arylene group having 6 to 30 carbon atomsfor forming a ring; n is an integer from 0 to 3; m is an integer from 0to 4; and n+m≧1.

In the material for an organic EL device according to an embodiment, asubstituted dibenzoheterole group with high electron tolerance isintroduced in (e.g., linked to) an amine group (or an amine compound),and the life of a layer utilizing the material for an organic EL devicemay increase, and the life of an organic EL device may increase. Sincethe dibenzoheterole group includes a substituent, the amorphousproperties of the material may be improved (e.g., the crystallinity ofthe material may be decreased), charge mobility may increase, and highemission efficiency may be realized.

In an embodiment, a compound represented by Formula 1 may be a compoundrepresented by Formula 2 or Formula 3.

In Formulae 2 and 3, X₂ is O or S; Ar₅ and Ar₆ are each independently asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms forforming a ring, a silyl group, a halogen atom, a deuterium atom, ahydrogen atom, or a substituted or unsubstituted dibenzoheterole grouphaving 10 to 30 carbon atoms for forming a ring and including an oxygenatom or a sulfur atom; Ar₇ and Ar₈ are each independently a silyl group,or a substituted or unsubstituted aryl group having 6 to 30 carbon atomsfor forming a ring; L₄ and L₅ are each independently a direct linkage,or a divalent group selected from a silyl group and a substituted orunsubstituted arylene group having 6 to 30 carbon atoms for forming aring; L₆ is a direct linkage or a divalent group selected from asubstituted or unsubstituted aryl group having 6 to 24 carbon atoms forforming a ring and a silyl group; R₁ to R₈ are each independently anaryl group having 6 to 30 carbon atoms for forming a ring, a heteroarylgroup having 5 to 30 carbon atoms for forming a ring, an alkyl grouphaving 1 to 15 carbon atoms, a silyl group, a halogen atom, a hydrogenatom or a deuterium atom; n is an integer from 0 to 3; m is an integerfrom 0 to 4; and n+m≧1.

In the material for an organic EL device according to an embodiment, inFormula 1, L₃ includes an m-phenylene group or a p-phenylene group, anda dibenzoheterole group is linked at the meta position or para positionof a phenylene group that is linked to an amine group. Thedibenzoheterole group is combined via a direct linkage or L₆ to thephenylene group. The molecular symmetry of the material may be broken,the amorphous properties of the material may be improved further, andcharge mobility may increase, thereby realizing the long life and highemission efficiency of an organic EL device.

In an embodiment, the compound represented by Formula 2 may be acompound represented by Formula 4.

In the material for an organic EL device according to an embodiment, inFormula 2, R₁ to R₄ are each independently a hydrogen atom, and the longlife and high efficiency of an organic EL device may be realized.

In an embodiment, the compound represented by Formula 4 may be acompound represented by Formula 5.

In the material for an organic EL device according to an embodiment, inFormula 4, L₄ and L₅ are each independently a direct linkage, Ar₈ is aphenyl group, m is 1, n is 0, and a dibenzoheterole group makes a bondwith an m-phenylene group at position 4. Since a part with high electrondensity of the dibenzoheterole group is substituted, the material may bestabilized, and the long life and high efficiency of an organic ELdevice may be realized.

In an embodiment, the compound represented by Formula 3 may be acompound represented by Formula 6.

In the material for an organic EL device according to an embodiment, inFormula 3, since each of R₅ to R₈ is a hydrogen atom, the long life andhigh efficiency of an organic EL device may be realized.

In an embodiment, the compound represented by Formula 6 may be acompound represented by Formula 7.

In the material for an organic EL device according to an embodiment, inFormula 6, each of L₄ and L₅ is a direct linkage, Ar₈ is a phenyl group,m is 1, n is 0, the dibenzoheterole group is combined with (e.g., bondedto) a p-phenylene group at position 4, and a part with high electrondensity of the dibenzoheterole group is substituted. Thus, the materialmay be stabilized, and the long life and high efficiency of an organicEL device may be realized.

According to an embodiment of the disclosure, an organic EL deviceincludes the material for an organic EL device in at least one layer ofa plurality of stacking layers between an emission layer and an anode.

In an embodiment, a first layer including the material for an organic ELdevice may be adjacent to the emission layer.

Since the first layer is disposed adjacent to the emission layer in theorganic EL device according to an embodiment, a hole transport layerdisposed between the first layer and the anode may be passivated fromelectrons not consumed in the emission layer, the diffusion of energywith an excited state generated in the emission layer into the holetransport layer may be prevented, and the charge balance of a wholedevice may be controlled. Thus, the increase of emission efficiency andlong life may be realized.

In an embodiment, the plurality of stacking layers may include a secondlayer including an electron accepting compound having a lowestunoccupied molecular orbital (LUMO) level within a range from about −9.0eV to about −4.0 eV, and the second layer may be between the anode andthe first layer.

Since the organic EL device according to an embodiment includes thesecond layer, hole injection properties from the anode may be improved,and emission efficiency may be improved.

In an embodiment, the plurality of stacking layers may include a thirdlayer including an amine derivative represented by Formula 8, and thethird layer may be between the first layer and the second layer.

In Formula 8, Ar₉, Ar₁₀ and Ar₁₁ are each independently a substituted orunsubstituted aryl group having 6 to 50 carbon atoms for forming a ring,or a substituted or unsubstituted heteroaryl group having 5 to 50 carbonatoms for forming a ring; Ar₁₂ is a substituted or unsubstituted arylgroup having 6 to 50 carbon atoms for forming a ring, a substituted orunsubstituted heteroaryl group having 5 to 50 carbon atoms for forming aring, or a substituted or unsubstituted alkyl group having 1 to 50carbon atoms; L₇ is a direct linkage, a substituted or unsubstitutedarylene group having 6 to 18 carbon atoms for forming a ring, or asubstituted or unsubstituted heteroarylene group having 5 to 15 carbonatoms for forming a ring.

Since the organic EL device according to an embodiment includes acompound having a carbazolyl group in a hole transport layer, holetransport properties and current flow durability may be improved, andemission efficiency and life may increase.

Since the organic EL device according to an embodiment utilizes thematerial for an organic EL device in at least one layer of a pluralityof stacking layers disposed between the emission layer and the anode,high emission efficiency and long life may be realized. For example,remarkable effects may be obtainable in from a green emission region toa blue emission region.

BRIEF DESCRIPTION OF THE FIGURES

The accompanying drawings are included to provide a furtherunderstanding of the disclosure, and are incorporated in and constitutea part of this specification. The drawings illustrate exampleembodiments of the disclosure and, together with the description, serveto explain principles of the disclosure. In the drawings:

FIG. 1 is a schematic diagram illustrating an organic EL device 100according to an embodiment;

FIG. 2 is a schematic diagram illustrating an organic EL device 200according to another embodiment;

FIG. 3 is a schematic diagram illustrating an organic EL device 300according to another embodiment; and

FIG. 4 is a schematic diagram illustrating an organic EL device 400according to another embodiment.

DETAILED DESCRIPTION

The inventors of the present disclosure thoroughly examined to solve theabove-described defects and found that high efficiency and long life maybe realized for a layer utilizing a material for an organic EL device,in which a substituted dibenzoheterole group with high electrontolerance is introduced in an amine group, thereby obtaining an organicEL device having high efficiency and long life.

Hereinafter, the material for an organic EL device and the organic ELdevice including the same according to an embodiment of the disclosurewill be described with reference to the accompanying drawings. Thematerial for an organic EL device and the organic EL device includingthe same according to an embodiment may, however, be embodied indifferent forms and should not be construed as limited to theembodiments set forth herein. In the drawings, like reference numeralsrefer to like elements or elements having like functions throughout, andrepeated explanation thereof will not be provided again.

The material for an organic EL device according to an embodiment is anamine compound including a substituted dibenzoheterole group representedby the following Formula 1.

In the material for an organic EL device of Formula 1 according to anembodiment, X₁ is O or S; Ar₁ and Ar₂ are each independently asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms forforming a ring, a silyl group, a halogen atom, a deuterium atom, ahydrogen atom, or a substituted or unsubstituted dibenzoheterole grouphaving 10 to 30 carbon atoms for forming a ring and including an oxygenatom or a sulfur atom; Ar₃ and Ar₄ are each independently a silyl group,or a substituted or unsubstituted aryl group having 6 to 30 carbon atomsfor forming a ring; L₁ and L₂ are each independently a direct linkage,or a divalent group selected from a silyl group and a substituted orunsubstituted arylene group having 6 to 30 carbon atoms for forming aring; L₃ is a divalent group selected from a silyl group and asubstituted or unsubstituted arylene group having 6 to 30 carbon atomsfor forming a ring; n is an integer from 0 to 3; m is an integer from 0to 4; and n+m≧1.

In the present disclosure, the term “substituted or unsubstituted” maycorrespond to an unsubstituted group; a group substituted with at leastone substituent selected from a deuterium atom, a halogen atom, anitrile group, a nitro group, an amino group, a phosphine oxide group,an alkoxy group, an aryloxy group, an alkylthioxy group, an arylthioxygroup, an alkylsulfoxy group, an arylsulfoxy group, a silyl group, aboron group, an alkyl group, a cycloalkyl group, an alkenyl group, anaryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, analkylamine group, a heteroarylamine group, an arylamine group and aheterocyclic group; or a group substituted with a substituent obtainedby connecting two or more substituents described above. For example, “asubstituent obtained by connecting two or more substituents” may be abiphenyl group. For example, the biphenyl group may be interpreted asthe aryl group or a substitutent obtained by connecting two or morephenyl groups.

In Formula 1, the aryl group having 6 to 30 carbon atoms for forming aring utilized as Ar₁ and Ar₂ may include a phenyl group, a naphthylgroup, an anthracenyl group, a phenanthryl group, a biphenyl group, aterphenyl group, a quaterphenyl group, a fluorenyl group, a triphenylenegroup, a biphenylene group, a pyrenyl group, a benzofluoranthenyl group,a chrysenyl group, a phenylnaphthyl group, a naphthylphenyl group, etc.,without being limited thereto.

The dibenzoheterole group having 10 to 30 carbon atoms for forming aring and including an oxygen atom or a sulfur atom utilized as Ar₁ andAr₂ may include a dibenzofuryl group, a dibenzothienyl group, etc.

The silyl group utilized as Ar₁ and Ar₂ may include a trialkylsilylgroup, a triarylsilyl group, a monoalkyldiarylsilyl group and adialkylmonoarylsilyl group, and may include, for example, atrimethylsilyl group, a triphenylsilyl group, etc.

The halogen atoms utilized as Ar₁ and Ar₂ may include a fluorine atom(F), a chlorine atom (Cl) and a bromine atom (Br).

In one embodiment, in Formula 1, an aryl group having 6 to 30 carbonatoms for forming a ring or a hydrogen atom may be utilized as Ar₁and/or Ar₂.

In Formula 1, the aryl group having 6 to 30 carbon atoms for forming aring utilized as Ar₃ and Ar₄ may be the same as the aryl group utilizedas Ar₁ and Ar₂. In addition, the silyl group utilized as Ar₃ and Ar₄ maybe the same as the silyl group utilized as Ar₁ and Ar₂.

In Formula 1, the arylene group having 6 to 30 carbon atoms for forminga ring among the divalent groups utilized as L₁ to L₃ may include aphenylene group, a biphenylene group, a terphenylene group, anaphthylene group, an anthracenyl group, a fluorenyl group, atriphenylene group, etc., without being limited thereto.

The divalent silyl group among the divalent groups utilized as L₁ to L₃may include a dimethylsilyl group and a diphenylsilylene group.

The substituents of the aryl group, the dibenzoheterole group includingan oxygen atom or a sulfur atom or the silyl group utilized as Ar₁ andAr₂, of the aryl group and the silyl group utilized as Ar₃ and Ar₄, andof the arylene group utilized as L₁ to L₃ may include a phenyl group, anaphthyl group, an anthracenyl group, a phenanthryl group, a biphenylgroup, a terphenyl group, a quaterphenyl group, a fluorenyl group, atriphenylene group, a biphenylene group, a pyrenyl group, abenzofluoranthenyl group, a chrysenyl group, a phenylnaphthyl group, anaphthylphenyl group, a trimethylsilyl group, a triphenylsilyl group, adibenzofuranyl group and a dibenzothiophenyl group. In one embodiment,the phenyl group, the naphthyl group, the biphenyl group, thephenylnaphthyl group, the naphthylphenyl group, the trimethylsilyl groupand the triphenylsilyl group may be utilized.

In the material for an organic EL device according to an embodiment, asubstituted dibenzoheterole group combined with (e.g., bonded to) thenitrogen atom (N) of the amine via L₃ is introduced. Since thesubstituted dibenzoheterole has high electron tolerance, thedeterioration of a material due to electrons not consumed in an emissionlayer may be restrained (e.g., reduced or prevented). In addition, sincethe dibenzoheterole group has a substituent, the amorphous properties ofthe material may be improved, and the mobility of charges may increase.Thus, the long life and high efficiency of the organic EL device may berealized.

In the material for an organic EL device according to an embodiment, anm-phenylene group or a p-phenylene group may be included in L₃ inFormula 1. The material for an organic EL device according to anembodiment may be an amine compound represented by the following Formula2 or Formula 3.

In the material for an organic EL device of Formula 2 and Formula 3according to an embodiment, X₂ is O or S; Ar₅ and Ar₆ are eachindependently a substituted or unsubstituted aryl group having 6 to 30carbon atoms for forming a ring, a substituted or unsubstituteddibenzoheterole group having 10 to 30 carbon atoms for forming a ringand including an oxygen atom or a sulfur atom, a silyl group, a halogenatom, a deuterium atom or a hydrogen atom; Ar₇ and Ar₈ are eachindependently a silyl group, or a substituted or unsubstituted arylgroup having 6 to 30 carbon atoms for forming a ring; L₄ and L₅ are eachindependently a direct linkage, or a divalent group selected from asilyl group and a substituted or unsubstituted arylene group having 6 to30 carbon atoms for forming a ring; L₆ is a direct linkage or a divalentgroup selected from a substituted or unsubstituted aryl group having 6to 24 carbon atoms for forming a ring and a silyl group, R₁ to R₈ areeach independently a substituted or unsubstituted aryl group having 6 to30 carbon atoms for forming a ring, a substituted or unsubstitutedheteroaryl group having 5 to 30 carbon atoms for forming a ring, analkyl group having 1 to 15 carbon atoms, a silyl group, a halogen atom,a hydrogen atom or a deuterium atom; n is an integer from 0 to 3; m isan integer from 0 to 4; and n+m≧1.

In Formulae 2 and 3, the aryl group having 6 to 30 carbon atoms forforming a ring, the dibenzoheterole group having 10 to 30 carbon atomsfor forming a ring and including an oxygen atom or a sulfur atom, thesilyl group and the halogen atom utilized as Ar₅ and Ar₆ may be the sameas the aryl group having 6 to 30 carbon atoms for forming a ring, thedibenzoheterole group having 10 to 30 carbon atoms for forming a ringand including an oxygen atom or a sulfur atom, the silyl group and thehalogen atom utilized as Ar₁ and Ar₂ in the compound represented byFormula 1.

In Formulae 2 and 3, Ar₅ and Ar₆ may be each independently an aryl grouphaving 6 to 30 carbon atoms for forming a ring or a hydrogen atom.

In Formulae 2 and 3, the aryl group having 6 to 30 carbon atoms forforming a ring utilized as Ar₇ and Ar₈ may be the same as the aryl grouputilized as Ar₁ and Ar₂ in the compound represented by Formula 1. Inaddition, the silyl group utilized as Ar₃ and Ar₄ may be the same as thesilyl group utilized as Ar₁ and Ar₂ in the compound represented byFormula 1.

In Formulae 2 and 3, the divalent group of the arylene group having 6 to30 carbon atoms for forming a ring and the silyl group utilized as L₄and L₅ may be the same as the divalent group of the arylene group andthe silyl group utilized as L₁ to L₃ in the compound represented byFormula 1.

In Formulae 2 and 3, the arylene group having 6 to 24 carbon atoms forforming a ring utilized as L₆ may include a phenylene group, abiphenylene group, a terphenylene group, a naphthylene group, ananthracenyl group, a fluorenylene group, a triphenylene group, etc.,without being limited thereto.

The divalent silyl group utilized as L₆ may be the same as the divalentsilyl group utilized as L₁ to L₃ in the compound represented by Formula1.

The aryl group having 6 to 30 carbon atoms for forming a ring utilizedas R₁ to R₈ in Formulae 2 and 3 may include a phenyl group, a naphthylgroup, an anthracenyl group, a phenanthryl group, a biphenyl group, aterphenyl group, a quaterphenyl group, a fluorenyl group, a triphenylenegroup, a biphenylene group, a pyrenyl group, a benzofluoranthenyl group,a chrysenyl group, a phenylnaphthyl group, a naphthylphenyl group, etc.,without being limited thereto.

In addition, the heteroaryl group having 5 to 30 carbon atoms forforming a ring utilized as R₁ to R₈ may include a pyridyl group, aquinolyl group, an isoquinolyl group, a benzofuryl group, a benzothienylgroup, an indolyl group, a benzoxazolyl group, a benzothiazolyl group, aquinoxalyl group, a benzoimidazolyl group, a dibenzofuryl group, adibenzothienyl group, a carbazolyl group, etc., without being limitedthereto.

The alkyl group having 1 to 15 carbon atoms utilized as R₁ to R₈ mayinclude a methyl group, an ethyl group, a propyl group, an isopropylgroup, an n-butyl group, an s-butyl group, an isobutyl group, a t-butylgroup, an n-pentyl group, an n-hexyl group, an n-heptyl group, ann-octyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a2-hydroxyethyl group, a 2-hydroxyisobutyl group, a 1,2-dihydroxyethylgroup, a 1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, a 1,2,3-trinitropropyl group, a cyclopropylgroup, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a1-norbornyl group, a 2-norbornyl group, etc.

In addition, the silyl group utilized as R₁ to R₈ may include atrialkylsilyl group, a triarylsilyl group, a monoalkyldiarylsilyl group,a dialkylmonoarylsilyl group, a trimethylsilyl group, a triphenylsilylgroup, etc.

In addition, the halogen atom utilized as R₁ to R₈ may include afluorine atom (F), a chlorine atom (Cl), a bromine atom (Br), etc.

In the material for an organic EL device according to an embodiment, anm-phenylene group or a p-phenylene group may be included in L₃ inFormula 1. Into the material for an organic EL device according to anembodiment represented by Formula 2 or 3, a dibenzoheterole group isintroduced at the meta position or the para position of a phenylenegroup combined with (e.g., bonded to) an amine group directly or via L₆.Thus, the symmetry of a molecule may be broken, and the amorphousproperties of the material may be improved further. Therefore, themobility of charges may increase, and the long life and high efficiencyof the organic EL device may be realized.

In the material for an organic EL device according to an embodiment,each of R₁ to R₄ in Formula 2 may be a hydrogen atom. That is, thematerial for an organic EL device according to an embodiment may be anamine compound represented by the following Formula 4.

By utilizing the a hydrogen atom atom for each of R₁ to R₄ in Formula 2of the material for an organic EL device according to an embodiment, thelong life and high efficiency of the organic EL device may be realized.

In the material for an organic EL device according to an embodiment, inFormula 4, L₄ and L₅ are each independently a direct linkage, Ar₈ is aphenyl group, m is 1, n is 0, and the dibenzoheterole group is combinedwith (e.g., bonded to) the m-phenylene group at position 4. The materialfor an organic EL device according to an embodiment may be an aminecompound represented by the following Formula 5.

In the material for an organic EL device according to an embodiment, inFormula 4, L₄ and L₅ are each independently a direct linkage, Ar₈ is aphenyl group, m is 1, n is 0, and the dibenzoheterole group is combinedwith (e.g., bonded to) the m-phenylene group at position 4. The position4 of the dibenzoheterole group is a part with high electron density andhigh reactivity. The compound may be stabilized by the substitution ofthe dibenzoheterole group at position 4 with high reactivity. Thus, thelong life of a layer utilizing the material for an organic EL deviceaccording to an embodiment may be realized, and the life of the organicEL device may increase further.

In the material for an organic EL device according to an embodiment,each of R₅ to R₈ in Formula 3 may be a hydrogen atom. The material foran organic EL device according to an embodiment may be an amine compoundrepresented by the following Formula 6.

In the material for an organic EL device according to an embodiment, inFormula 3, each of R₅ to R₈ is a hydrogen atom, and the long life andhigh efficiency of the organic EL device may be realized.

In the material for an organic EL device according to an embodiment, inFormula 6, L₄ and L₅ are each independently a direct linkage, Ar₈ is aphenyl group, m is 1, n is 0, and the dibenzoheterole group is combinedwith (e.g., bonded to) the p-phenylene group at position 4. The materialfor an organic EL device according to an embodiment may be an aminecompound represented by the following Formula 7.

According to an embodiment, the material for an organic EL devicerepresented by Formula 6 may be stabilized if L₄ and L₅ are eachindependently a direct linkage, Ar₈ is a phenyl group, m is 1, n is 0,and the dibenzoheterole group is combined with (e.g., bonded to) thep-phenylene group at position 4. Thus, the long life of a layerutilizing the material for an organic EL device according to anembodiment may be realized, and the increase of the life of the organicEL device may be realized.

The material for an organic EL device according to an embodiment mayinclude at least one of compounds in Compounds group 1 (includingcompounds 1 to 269 and 300 to 311) below.

The material for an organic EL device according to an embodiment may beutilized in at least one layer of stacking layers (e.g., utilized in atleast one layer of a plurality of layers stacked over one another)disposed between an emission layer and an anode of an organic EL device.As described above, in the material for an organic EL device accordingto an embodiment, a substituted dibenzoheterole group with high electrontolerance is introduced in (e.g., linked to) the nitrogen atom (N) of anamine group via a linker. Thus, the electron tolerance of a layerutilizing the material for an organic EL device according to anembodiment may be improved, the durability thereof may be improved, andthe long life of the organic EL device may be realized. Since thedibenzoheterole group includes a substituent, the amorphous propertiesof the material may be improved, the mobility of charges may increase,and high emission efficiency may be realized.

The layer including the material for an organic EL device according toan embodiment may be a layer disposed adjacent to the emission layeramong stacking layers disposed between the emission layer and the anodeof the organic EL device. Since the layer including the material for anorganic EL device according to an embodiment is disposed adjacent to theemission layer, the deterioration of the layer disposed between thelayer including the material for an organic EL device according to anembodiment and the anode due to electrons may be restrained (e.g.,reduced or prevented).

(Organic EL Device 1)

An organic EL device utilizing a material for an organic EL deviceaccording to an embodiment of the disclosure will be explained. FIG. 1is a schematic diagram illustrating an organic EL device 100 accordingto an embodiment of the disclosure. The organic EL device 100 mayinclude, for example, a substrate 102, an anode 104, a hole injectionlayer 106, a hole transport layer 108, an emission layer 110, anelectron transport layer 112, an electron injection layer 114 and acathode 116. In an embodiment, the material for an organic EL deviceaccording to an embodiment of the disclosure may be utilized in at leastone layer of stacking layers disposed between the emission layer and theanode.

A case that the material for an organic EL device according to thedisclosure is utilized in the hole transport layer 108 will be explainedas an embodiment.

The substrate 102 may be a transparent glass substrate, a semiconductorsubstrate formed utilizing silicon, or a flexible substrate of a resin,etc.

The anode 104 may be disposed on the substrate 102 and may be formedutilizing indium tin oxide (ITO), indium zinc oxide (IZO), etc.

The hole injection layer (HIL) 106 may be formed utilizing a suitablematerial to a thickness within a range from about 10 nm to about 150 nm.For example, triphenylamine-containing poly ether ketone (TPAPEK),4-isopropyl-4′-methyldiphenyliodoniumtetrakis(pentafluorophenyl)borate(PPBI),N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-trile-amino)-phenyl]-biphenyl-4,4′-diamine(DNTPD), a phthalocyanine compound (such as copper phthalocyanine)suitable, 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine(m-MTDATA), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB),4,4′,4″-tris{N,N-diphenylamino}triphenylamine (TDATA),4,4′,4″-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate (PEDOT/PSS),polyaniline/camphorsulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), etc., may be included.

The hole transport layer (HTL) 108 may be formed on the hole injectionlayer 106 utilizing the material for an organic EL device according tothe disclosure to a thickness within a range from about 10 nm to about150 nm. The hole transport layer 108 including the material for anorganic EL device according to the disclosure may be formed by a vacuumevaporation method.

The emission layer (EL) 110 may be formed on the hole transport layer108 utilizing a suitable host material to a thickness within a rangefrom about 10 nm to about 60 nm. The suitable host material utilized inthe emission layer 110 may include, for example,tris(8-quinolinolato)aluminum (Alq3), 4,4′-N,N′-dicarbazole-biphenyl(CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene(ADN), 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI),3-tert-butyl-9,10-di(naphtho-2-yl)anthracene (TBADN), distyrylarylene(DSA), 4,4′-bis(9-carbazole)-2,2′-dimethyl-biphenyl (dmCBP), etc.

The host material utilized in the emission layer 110 may be selectedfrom an anthracene derivative, a pyrene derivative, a fluoranthenederivative, a chrysene derivative, a benzoanthracene derivative and atriphenylene derivative. In one embodiment, the emission layer 110 mayinclude the anthracene derivative or the pyrene derivative. As theanthracene derivative utilized in the emission layer 110, a compoundrepresented by the following Formula 9 may be utilized.

In Formula 9, R₁₁ to R₂₀ are each independently a substituted orunsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,a substituted or unsubstituted heteroaryl group having 1 to 30 carbonatoms for forming a ring, an alkyl group having 1 to 15 carbon atoms, asilyl group, a halogen atom, a hydrogen atom or a deuterium atom. Inaddition, g and h are each independently an integer from 0 to 5. Aplurality of adjacent R₁₁ to R₂₀ may make a bond to form a saturated orunsaturated ring.

The substituted or unsubstituted heteroaryl group having 1 to 30 carbonatoms for forming a ring utilized as R₁₁ to R₂₀ may include abenzothiazolyl group, a thiophenyl group, a thienothiophenyl group, athienothienothiophenyl group, a benzothiophenyl group, a benzofurylgroup, a dibenzothiophenyl group, a dibenzofuryl group, an N-arylcarbazolyl group, an N-heteroarylcarbazolyl group, an N-alkylcarbazolylgroup, a phenoxazinyl group, a phenothiazyl group, a pyridyl group, apyrimidyl group, a triazile group, a quinolinyl group, a quinoxalylgroup, etc., without being limited thereto.

The substituted or unsubstituted heteroaryl group having 1 to 30 carbonatoms for forming a ring utilized as R₁₁ to R₂₀ may include abenzothiazolyl group, a thiophenyl group, a thienothiophenyl group, athienothienothiophenyl group, a benzothiophenyl group, a benzofurylgroup, a dibenzothiophenyl group, a dibenzofuryl group, an N-arylcarbazolyl group, an N-heteroarylcarbazolyl group, an N-alkylcarbazolylgroup, a phenoxazinyl group, a phenothiazyl group, a pyridyl group, apyrimidyl group, a triazile group, a quinolinyl group, a quinoxalylgroup, etc., without being limited thereto.

The alkyl group having 1 to 15 carbon atoms utilized as R₁₁ to R₂₀ mayinclude a methyl group, an ethyl group, a propyl group, an isopropylgroup, an n-butyl group, an s-butyl group, an isobutyl group, a t-butylgroup, an n-pentyl group, an n-hexyl group, an n-heptyl group, ann-octyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a2-hydroxyethyl group, a 2-hydroxyisobutyl group, a 1,2-dihydroxyethylgroup, a 1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, a 1,2,3-trinitropropyl group, a cyclopropylgroup, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a1-norbornyl group, a 2-norbornyl group, etc., without being limitedthereto.

The anthracene derivative utilized in the emission layer 110 of theorganic EL device according to an embodiment may include at least one ofcompounds a-1 to a-12 below.

The emission layer 110 may include, as a dopant material, styrylderivatives (such as 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene(BCzVB), 4-(di-p-tolylamino)-4′-[(di-p-tolylamino)styryl]stilbene(DPAVB), orN-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl)phenyl-N-phenylbenzeneamine(N-BDAVBI)), perylene and the derivatives thereof (such as2,5,8,11-tetra-t-butylperylene (TBPe)), pyrene and the derivativesthereof (such as 1,1-dipyrene, 1,4-dipyrenylbenzene, or1,4-bis(N,N-diphenylamino)pyrene), etc., without being limited thereto.

The electron transport layer (ETL) 112 may be formed on the emissionlayer 110 to a thickness within a range from about 15 nm to about 50 nmutilizing tris(8-hydroxyquinolinato)aluminum (Alq3) or a material havinga nitrogen-containing aromatic ring (for example, a material including apyridine ring such as 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, amaterial including a triazine ring such as2,4,6-tris(3′-(pyridine-3-yl)biphenyl-3-yl)1,3,5-triazine, and amaterial including an imidazole derivative such as2-(4-N-phenylbenzoimidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene).

The electron injection layer (EIL) 114 may be formed on the electrontransport layer 112 to a thickness within a range from about 0.3 nm toabout 9 nm utilizing a material including, for example, lithium fluoride(LiF), lithium-8-quinolinato (Liq), etc.

The cathode 116 may be disposed on the electron injection layer 114 andmay be formed utilizing a metal (such as aluminum (Al), silver (Ag),lithium (Li), magnesium (Mg), calcium (Ca), or a mixture thereof) and atransparent material (such as ITO or IZO).

Each electrode and each layer constituting the organic EL deviceaccording to the disclosure as described above may be formed byselecting an appropriate layer forming method depending on a materialutilized, such as a vacuum evaporation method, a sputtering method, orvarious suitable coating methods. The hole transport layer 108 formedutilizing the material for an organic EL device according to thedisclosure may be formed by the vacuum evaporation method.

In the organic EL device 100 according to the disclosure, a holetransport layer capable of realizing long life and high efficiency maybe formed utilizing the material for an organic EL device according tothe disclosure.

In the organic EL device 100 according to the disclosure, the materialfor an organic EL device according to the disclosure may be utilized asthe material of the hole injection layer. As described above, an organicEL device with long life and high efficiency may be manufactured byutilizing the material for an organic EL device according to thedisclosure in at least one layer of stacking layers disposed between theemission layer and the anode.

(Organic EL Device 2)

Another organic EL device utilizing a material for an organic EL deviceaccording to an embodiment of the disclosure will be explained. FIG. 2is a schematic diagram illustrating an organic EL device 200 accordingto another embodiment of the disclosure. In FIG. 2, the same referencenumerals may be designated to the same parts or parts havingsubstantially the same function as those in the organic EL device 100shown in FIG. 1, and repeated explanation thereof will not be providedagain.

The organic EL device 200 may include a substrate 102, an anode 104, ahole transport band 201, an emission layer 110, an electron transportlayer 112, an electron injection layer 114 and a cathode 116. The holetransport band 201 may include a first layer 203 disposed at theanode-side and a second layer 207 disposed between the first layer 203and the emission layer 110. In the hole transport band 201, a thirdlayer 205 may be disposed between the anode 104 and the second layer207. The position of the third layer 205 is not specifically limited,however, and it may be disposed between the first layer 203 and thesecond layer 207. In the hole transport band 201, another hole transportlayer may be disposed between the first layer 203 and the third layer205, and between the third layer 205 and the second layer 207. In theorganic EL device 200, the material for an organic EL device may beappropriately utilized in the second layer 207 adjacent to the emissionlayer 110.

The first layer 203 disposed at the anode side of the hole transportband 201 may include an electron accepting compound having a LUMO levelwithin a range from about −9.0 eV to about −4.0 eV. The first layer 203may be formed utilizing a hole transport compound doped with theelectron accepting compound or may be formed utilizing only the electronaccepting compound. Examples of the electron accepting compound may beat least one of compounds ac1 to ac14. However, the electron acceptingcompound according to the disclosure is not limited thereto.

In the electron accepting Compounds ad to ac14, R is a hydrogen atom, adeuterium atom, a halogen atom, a fluoroalkyl group having 1 to 10carbon atoms, a cyano group, an alkoxy group having 1 to 10 carbonatoms, an alkyl group having 1 to 10 carbon atoms, or a substituted orunsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.However, all Rs may not be (e.g., at least one of the Rs is not) ahydrogen atom, a deuterium atom or fluorine in a molecule. Ar is eachindependently a substituted aryl group with an electron withdrawinggroup or an unsubstituted aryl group having 6 to 30 carbon atoms forforming a ring, or a substituted or unsubstituted heteroaryl grouphaving 3 to 30 carbon atoms for forming a ring; Y is a methine group(—CH═) or a nitrogen atom (—N═); Z is a pseudohalogen atom or a sulfur(S) atom; and X is one of the substituents represented by the followingformulae X₁ to X₇.

In Formulae X5 to X7, Ra is a hydrogen atom, a deuterium atom, a halogenatom, a fluoroalkyl group having 1 to 10 carbon atoms, a cyano group, analkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms for forming a ring or a substituted or unsubstitutedheteroaryl group having 3 to 30 carbon atoms for forming a ring.

Examples of the substituted or unsubstituted aryl group having 6 to 30carbon atoms for forming a ring, or the substituted or unsubstitutedheteroaryl group having 3 to 30 carbon atoms for forming a ring,represented by R, Ar and Ra, may include a phenyl group, a 1-naphthylgroup, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylylgroup, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-ylgroup, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, anm-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-ylgroup, an o-tolyl group, an m-tolyl group, a p-tolyl group, ap-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, a4″-t-butyl-p-terphenyl-4-yl group, a fluoranthenyl group, a fluorenylgroup, a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, apyridinyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinylgroup, a 1-indolyl group, a 2-indolyl group, a 3-indolyl group, a4-indolyl group, a 5-indolyl group, a 6-indolyl group, a 7-indolylgroup, a 1-isoindolyl group, a 2-isoindolyl group, a 3-isoindolyl group,a 4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group, a7-isoindolyl group, a 2-furyl group, a 3-furyl group, a 2-benzofuranylgroup, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranylgroup, a 6-benzofuranyl group, a 7-benzofuranyl group, a1-isobenzofuranyl group, a 3-isobenzofuranyl group, a 4-isobenzofuranylgroup, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a7-isobenzofuranyl group, a quinolyl group, a 3-quinolyl group, a4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolylgroup, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolylgroup, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinylgroup, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolylgroup, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group,a 9-carbazolyl group, a 1-phenanthridinyl group, a 2-phenanthridinylgroup, a 3-phenanthridinyl group, a 4-phenanthridinyl group, a6-phenanthridinyl group, a 7-phenanthridinyl group, an 8-phenanthridinylgroup, a 9-phenanthridinyl group, a 10-phenanthridinyl group, a1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group, a4-acridinyl group, a 9-acridinyl group, a 1,7-phenanthroline-2-yl group,a 1,7-phenanthroline-3-yl group, a 1,7-phenanthroline-4-yl group, a1,7-phenanthroline-5-yl group, a 1,7-phenanthroline-6-yl group, a1,7-phenanthroline-8-yl group, a 1,7-phenanthroline-9-yl group, a1,7-phenanthroline-10-yl group, a 1,8-phenanthroline-2-yl group, a1,8-phenanthroline-3-yl group, a 1,8-phenanthroline-4-yl group, a1,8-phenanthroline-5-yl group, a 1,8-phenanthroline-6-yl group, a1,8-phenanthroline-7-yl group, a 1,8-phenanthroline-9-yl group, a1,8-phenanthroline-10-yl group, a 1,9-phenanthroline-2-yl group, a1,9-phenanthroline-3-yl group, a 1,9-phenanthroline-4-yl group, a1,9-phenanthroline-5-yl group, a 1,9-phenanthroline-6-yl group, a1,9-phenanthroline-7-yl group, a 1,9-phenanthroline-8-yl group, a1,9-phenanthroline-10-yl group, a 1,10-phenanthroline-2-yl group, a1,10-phenanthroline-3-yl group, a 1,10-phenanthroline-4-yl group, a1,10-phenanthroline-5-yl group, a 2,9-phenanthroline-1-yl group, a2,9-phenanthroline-3-yl group, a 2,9-phenanthroline-4-yl group, a2,9-phenanthroline-5-yl group, a 2,9-phenanthroline-6-yl group, a2,9-phenanthroline-7-yl group, a 2,9-phenanthroline-8-yl group, a2,9-phenanthroline-10-yl group, a 2,8-phenanthroline-1-yl group, a2,8-phenanthroline-3-yl group, a 2,8-phenanthroline-4-yl group, a2,8-phenanthroline-5-yl group, a 2,8-phenanthroline-6-yl group, a2,8-phenanthroline-7-yl group, a 2,8-phenanthroline-9-yl group, a2,8-phenanthroline-10-yl group, a 2,7-phenanthroline-1-yl group, a2,7-phenanthroline-3-yl group, a 2,7-phenanthroline-4-yl group, a2,7-phenanthroline-5-yl group, a 2,7-phenanthroline-6-yl group, a2,7-phenanthroline-8-yl group, a 2,7-phenanthroline-9-yl group, a2,7-phenanthroline-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 10-phenothiazinylgroup, a 1-phenoxaziny group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 10-phenoxazinyl group, a 2-oxazolylgroup, a 4-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a5-oxadiazolyl group, a 3-furazanyl group, a 2-thienyl group, a 3-thienylgroup, a 2-methylpyrrole-1-yl group, a 2-methylpyrrole-3-yl group, a2-methylpyrrole-4-yl group, a 2-methylpyrrole-5-yl group, a3-methylpyrrole-1-yl group, a 3-methylpyrrole-2-yl group, a3-methylpyrrole-4-yl group, a 3-methylpyrrole-5-yl group, a2-t-butylpyrrole-4-yl group, a 3-(2-phenylpropyl)pyrrole-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a2-t-butyl-1-indolyl group, a 4-t-butyl-1-indolyl group, a2-t-butyl-3-indolyl group, a 4-t-butyl-3-indolyl group, etc.

Examples of the fluoroalkyl group having 1 to 10 carbon atomsrepresented by R and Ra may include a perfluoroalkyl group (such as atrifluoromethyl group, a pentafluoroethyl group, a heptafluoropropylgroup or a heptadecafluorooctane group), a monofluoromethyl group, adifluoromethyl group, a trifluoroethyl group, a tetrafluoropropyl group,an octafluoropentyl group, etc.

Examples of the alkyl group having 1 to 10 carbon atoms represented by Rand Ra may include a methyl group, an ethyl group, a propyl group, anisopropyl group, an n-butyl group, an s-butyl group, an isobutyl group,a t-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group,an n-octyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a2-hydroxyethyl group, a 2-hydroxyisobutyl group, a 1,2-dihydroxyethylgroup, a 1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, a 1,2,3-trinitropropyl group, a cyclopropylgroup, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a1-norbornyl group, a 2-norbornyl group, etc.

The alkoxy group having 1 to 10 carbon atoms represented by R and Ra maybe a group represented by —OY. Examples of Y may include a methyl group,an ethyl group, a propyl group, an isopropyl group, an n-butyl group, ans-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, ann-hexyl group, an n-heptyl group, an n-octyl group, a hydroxymethylgroup, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, a 1,2,3-trinitropropyl group, etc.

Examples of the halogen atom represented by R and Ra may includefluorine, chlorine, bromine and iodine.

In the case that the electron accepting compound is doped in anotherhole transport compound, a suitable hole transport compound may beutilized as the hole transport compound included in the first layer 203.As the suitable hole transport compound, a compound having a carbazolylgroup may be utilized, without being limited thereto. The hole transportcompound having the carbazolyl group may be, for example, an aminederivative represented by the following Formula 8.

In Formula 8, Ar₉, Ar₁₀ and Ar₁₁ are each independently a substituted orunsubstituted aryl group having 6 to 50 carbon atoms for forming a ring,or a substituted or unsubstituted heteroaryl group having 5 to 50 carbonatoms for forming a ring; Ar₁₂ is a substituted or unsubstituted arylgroup having 6 to 50 carbon atoms for forming a ring, a substituted orunsubstituted heteroaryl group having 5 to 50 carbon atoms for forming aring, or a substituted or unsubstituted alkyl group having 1 to 50carbon atoms; and L₇ is a direct linkage, a substituted or unsubstitutedarylene group having 6 to 18 carbon atoms for forming a ring, or asubstituted or unsubstituted heteroarylene group having 5 to 15 carbonatoms for forming a ring.

In one embodiment, Ar₉ to Ar₁₁ may be each independently a phenyl group,a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group,a phenanthryl group, a fluorenyl group, an indenyl group, a pyranylgroup, an acetonaphthenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyridyl group, a pyranyl group, a quinolyl group, anisoquinolyl group, a benzofuranyl group, a benzothienyl group, anindolyl group, a carbazolyl group, a benzoxazolyl group, abenzothiazolyl group, a quinoxalyl group, a benzoimidazolyl group, adibenzofuranyl group, a dibenzothienyl group, etc. For example, thephenyl group, the biphenyl group, the terphenyl group, the fluorenylgroup, the carbazolyl group, the dibenzofuranyl group, etc. may beutilized.

As Ar₁₂, the aryl group and the heteroaryl group may be the same as thefunctional groups exemplified as Ar₉ to Ar₁₁, and the alkyl group maybe, for example, a methyl group or an ethyl group.

L₇ may include, other than the direct linkage, a phenylene group, abiphenylylene group, a terphenylylene group, a naphthylene group, ananthrylene group, a phenanthrylene group, a fluorelene group, anindandiyl group, a pyrenediyl group, an acenaphthenediyl group, afluoranthenediyl group, a triphenylenediyl group, a pyridinediyl group,a pyranediyl group, a quinolinediyl group, an isoquinolinediyl group, abenzofurandiyl group, a benzothiophenediyl group, an indolediyl group, acarbazolediyl group, a benzoxazolediyl group, a benzothiazolediyl group,a quinoxalinediyl group, a benzoimidazolediyl group, a dibenzofuranediylgroup, etc. For example, the phenylene group, the terphenylene group,the fluorenediyl group, the carbazolediyl group, the dibenzofuranediyl,etc. may be utilized.

The compound represented by Formula 8 may include at least one of thecompounds 270 to 285.

In the hole transport band 201, the third layer 205 may include acompound represented by Formula 8. The compound represented by Formula 8and included in the third layer 205 may be Compounds 270 to 285.

Each electrode and each layer constituting the organic EL device 200according to the disclosure as described above may be formed byselecting an appropriate layer forming method depending on materialsutilized, such as a vacuum evaporation method, a sputtering method orvarious suitable coating methods. In addition, the second layer 207formed utilizing the material for an organic EL device according to thedisclosure may be formed by the vacuum evaporation method.

In the hole transport band 201 in the organic EL device 200, at leastone of the first layer 203 including an electron accepting compoundhaving a LUMO level within a range from about −9.0 eV to about −4.0 eVis disposed adjacent to the anode 104, and at least one of the secondlayer 207 including the material for an organic EL device according toan embodiment is disposed adjacent to the emission layer 110. Theorganic EL device 200 according to an embodiment includes the materialfor an organic EL device according to an embodiment with high electrontolerance and improved amorphous properties in the hole transport secondlayer 207 disposed adjacent to the emission layer 110 in the holetransport band 201, and the hole transport layer between the anode 104and the second layer 207 may be passivated from electrons not consumedin the emission layer 110. In addition, the diffusion of energy with anexcited state generated in the emission layer 110 into the holetransport layer between the anode 104 and the second layer 207 may bereduced or prevented, and the charge balance of the whole organic ELdevice 200 may be adjusted. By disposing the second layer 207 includingthe material for an organic EL device adjacent to the emission layer110, the diffusion of the electron accepting compound included in thefirst layer 203 into the emission layer 110 may be restrained.

According to an embodiment, as the material for an organic EL deviceincluded in the second layer 207, a compound of Formula 1, in which adibenzoheterole group is dibenzofuran, L₃ includes an m-phenylene groupor a p-phenylene group, and an amine group includes a substituent of anaphthyl group, a biphenyl group or a naphthyl phenyl group, isutilized. According to another embodiment, as the material for anorganic EL device included in the second layer 207, a compoundrepresented by Formula 4 or 6 and includes an amine group having asubstituent of a naphthyl group, a biphenyl group or a naphthyl phenylgroup may be utilized.

In the organic EL device 200, the first layer 203 including the electronaccepting compound may be disposed near the anode 104, for example,adjacent to (e.g., in contact with) the anode 104. By disposing a layerincluding the electron accepting compound adjacent to the anode 104, thehole injection properties from the anode 104 may be improved. In thecase that a hole transport compound having a carbazolyl group,represented by Formula 8, is included in the first layer 203, chargetransport properties and current flow durability may be improved.

In the organic EL device 200, the third layer 205 including a compoundhaving a carbazolyl group and represented by Formula 8 may be disposednearer to the emission layer 110 than to the first layer 203. Byincluding the compound having the carbazolyl group in the hole transportband 201, charge transport properties and current flow durability may beimproved. In addition, since the third layer 205 includes the compoundrepresented by Formula 8, the hole transport layer between the anode 104and the third layer 205 may be passivated from electrons not consumed inthe emission layer 110, and the diffusion of energy with an excitedstate generated in the emission layer 110 into the hole transport layerbetween the anode 104 and the third layer 205 may be reduced orprevented. In addition, the compound represented by Formula 8, which isan amine derivative having a carbazolyl group may restrain (e.g., reduceor prevent) the diffusion of the electron accepting compound included inthe first layer 203 into the emission layer 110.

In the organic EL device 200 according to an embodiment, the materialfor an organic EL device according to an embodiment may be utilized asthe material of the second layer 207 adjacent to the emission layer 110,the first layer 203 including the electron accepting compound may bedisposed adjacent to the anode 104, and the third layer 205 includingthe compound represented by Formula 8 may be disposed between the firstlayer 203 and the second layer 207. Thus, the high efficiency and longlife of the organic EL device may be realized.

The material for an organic EL device according to an embodiment may beapplied in an organic EL display of an active matrix type utilizing athin film transistor (TFT).

(Manufacturing Method)

The material for an organic EL device according to an embodiment may besynthesized, for example, as follows.

Synthetic Method of Compound 17

(Synthesis of Compound A in Formula 14)

First, the following Compound A was synthesized. Under an Ar atmosphere,53.8 g ofN-[1,1′-biphenyl]-4-yl-N-(4-bromophenyl)-[1,1′-biphenyl]-4-amine, 6.46 gof Pd(dppf)Cl₂.CH₂Cl₂, 33.3 g of KOAc and 33.0 g ofbis(pinacolato)diboron were added to a 2 L flask, followed by degassingunder vacuum in a dioxane solvent and stirring at about 100° C. forabout 12 hours. After that, the solvent was distilled, CH₂Cl₂ and waterwere added thereto, an organic phase was separated, magnesium sulfateand activated clay were added thereto (e.g, added to the organic phase),filtering with suction was performed, and the solvents were distilled.The crude product thus obtained was separated by silica gel columnchromatography (utilizing a mixture solvent of dichloromethane andhexane) to produce 56.8 g of Compound A as a white solid (Yield 98%).The molecular weight of Compound A measured by FAB-MS was 523.

Synthesis of Compound B in Formula 15

Then, the following Compound B was synthesized. Under an Ar atmosphere,10.0 g of Compound A, 6.00 g of 1-iodo-3-bromobenzene, 1.54 g ofPd(PPh₃)₄ and 5.25 g of potassium carbonate were added to a 300 ml,three necked flask, followed by heating and stirring in a mixturesolvent of 450 mL of toluene and 60 mL of water at about 90° C. forabout 8 hours. After air cooling, water was added, an organic layer wasseparated, and the solvents were distilled. The crude product thusobtained was separated by silica gel column chromatography (utilizing amixture solvent of dichloromethane and hexane) and recrystallizedutilizing a mixture solvent of toluene and hexane to produce 9.29 g ofCompound B as a white solid (Yield 87%). The molecular weight ofCompound B measured by FAB-MS was 553.

(Synthesis of Compound C in Formula 16)

Then, the following Compound C was synthesized. Substantially the sameprocedure as that of the method for synthesizing Compound A wasconducted except for utilizing 4.00 g of Compound B instead ofN-[1,1′-biphenyl]-4-yl-N-(4-bromophenyl)-[1,1′-biphenyl]-4-amine toproduce 4.12 g of Compound C as a pale yellow solid (Yield 95%). Themolecular weight of Compound C measured by FAB-MS was 599.

(Synthesis of Compound D in Formula 17)

The following Compound D was synthesized. Under an Ar atmosphere, 2.70 gof Compound C, 3.70 g of 4,6-dibromodibenzofuran, 0.34 g of Pd(PPh₃)₄and 1.25 g of potassium carbonate were added to a 300 ml, three neckedflask, followed by heating and stirring in a mixture solvent of 50 mL oftoluene and 20 mL of water at about 90° C. for about 8 hours. After aircooling, water was added, an organic layer was separated, and thesolvents were distilled. The crude product thus obtained was separatedby silica gel column chromatography (utilizing a mixture solvent ofdichloromethane and hexane) and recrystallized utilizing a mixturesolvent of toluene and hexane to produce 1.78 g of Compound D as a whitesolid (Yield 55%). The molecular weight of Compound D measured by FAB-MSwas 686.

(Synthesis of Compound 17 in Formula 18)

Under an Ar atmosphere, 7.18 g of Compound D, 2.10 g of phenylboronicacid, 1.14 g of Pd(PPh₃)₄ and 3.55 g of potassium carbonate were addedto a 300 ml, three necked flask, followed by heating and stirring in amixture solvent of 150 mL of toluene and 60 mL of water at about 90° C.for about 8 hours. After air cooling, water was added, an organic layerwas separated, and the solvents were distilled. The crude product thusobtained was separated by silica gel column chromatography (utilizing amixture solvent of dichloromethane and hexane) and recrystallizedutilizing a mixture solvent of toluene and hexane to produce 6.79 g ofCompound 17 as a white solid (Yield 95%).

The molecular weight of Compound 17 measured by FAB-MS was 715. Thechemical shift values (δ) of Compound 17 measured by ¹H-NMR (CDCl₃) were7.85 (d, 2H, J=7.80 Hz), 7.81 (d, 2H, J=7.90 Hz), 7.70 (s, 1H),7.58-7.50 (m, 19H), 7.48-7.41 (m, 7H), 6.69-6.65 (m, 6H)).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthetic Method of Compound 5

Compound 5 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 17 except for utilizing4,6-dibromodibenzothiophene instead of 4,6-dibromodibenzofuran. Themolecular weight of Compound 5 measured by FAB-MS was 732. The chemicalshift values (δ) of Compound 5 measured by ¹H-NMR (CDCl₃) were 7.89 (d,2H, J=7.90 Hz), 7.83 (d, 2H, J=7.70 Hz), 7.72 (s, 1H), 7.68-7.55 (m,19H), 7.48-7.41 (m, 7H), 6.71-6.67 (m, 6H). From the results, thesynthesized white solid was determined as Compound 5.

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthetic Method of Compound 77

Compound 77 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 17 except for utilizing2,8-dibromodibenzothiophene instead of 4,6-dibromodibenzofuran. Themolecular weight of Compound 77 measured by FAB-MS was 732. The chemicalshift values (δ) of Compound 77 measured by ¹H-NMR (CDCl₃) were 7.80 (d,2H, J=7.90 Hz), 7.73 (d, 2H, J=7.70 Hz), 7.70 (d, 2H, J=7.90 Hz), 7.79(s, 1H), 7.64-7.55 (m, 17H), 7.48-7.41 (m, 7H), 6.71-6.67 (m, 6H). Fromthe results, the synthesized white solid was determined as Compound 77.

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthetic Method of Compound 89

Compound 89 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 17 except for utilizing2,8-dibromodibenzofuran instead of 4,6-dibromodibenzofuran. Themolecular weight of Compound 89 measured by FAB-MS was 715. The chemicalshift values (δ) of Compound 89 measured by ¹H-NMR (CDCl₃) were 7.82 (d,2H, J=7.84 Hz), 7.78 (d, 2H, J=7.90 Hz), 7.70 (d, 2H, J=7.88 Hz), 7.68(s, 1H), 7.66-7.57 (m, 17H), 7.51-7.41 (m, 7H), 6.68-6.64 (m, 6H). Fromthe results, the synthesized white solid was determined as Compound 89.

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthetic Method of Compound 141

Compound 141 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 17 except for utilizing3,7-dibromodibenzofuran instead of 4,6-dibromodibenzofuran. Themolecular weight of Compound 141 measured by FAB-MS was 715. Thechemical shift values (δ) of Compound 141 measured by ¹H-NMR (CDCl₃)were 7.95 (d, 2H, J=7.80 Hz), 7.75 (d, 2H, J=7.70 Hz), 7.70 (s, 1H),7.64 (d, 2H, J=7.90 Hz), 7.57-7.51 (m, 19H), 7.48-7.40 (m, 5H),6.72-6.65 (m, 6H). From the results, the synthesized white solid wasdetermined as Compound 141.

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthetic Method of Compound 213

(Synthesis of Compound F in Formula 19)

First, the following Compound F was synthesized. Under an Ar atmosphere,30.0 g of Compound E, 16.4 g of4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 4.34 g ofPd(PPh₃)₄ and 31.8 g of K₃PO₄ were added to a 1,000 mL, three neckedflask, followed by heating and stirring in a mixture solvent of 400 mLof toluene and 70 mL of water at about 80° C. for about 8 hours. Afterair cooling, water was added, an organic layer was separated, and thesolvents were distilled. The crude product thus obtained was separatedby silica gel column chromatography (utilizing a mixture solvent ofdichloromethane and hexane) and recrystallized utilizing a mixturesolvent of toluene and acetonitrile to produce 27.7 g of Compound F as ayellow solid (Yield 90%). The molecular weight of Compound F measured byFAB-MS was 411.

(Synthesis of Compound G in Formula 20)

The following Compound G was synthesized. Under an Ar atmosphere, 25.0 gof Compound F, 14.2 g of 4-bromobiphenyl, 1.99 g of Pd₂(dba)₃, 1.20 g oftri-tert-butylphosphine, and 8.89 g of NaOtBu were added to a 1,000 mL,three necked flask, followed by heating, refluxing and stirring in 300mL of a mixture solvent of toluene for about 8 hours (or about 6 hours).After air cooling, water was added, an organic layer was separated, andthe solvents were distilled. The crude product thus obtained wasseparated by silica gel column chromatography (utilizing a mixturesolvent of dichloromethane and hexane) and recrystallized utilizing amixture solvent of toluene and ethanol to produce 17.5 g of Compound Gas a yellow solid (Yield 51%). The molecular weight of Compound Gmeasured by FAB-MS was 564.

(Synthesis of Compound 213 in Formula 21)

Under an Ar atmosphere, 4.00 g of Compound G, 2.0 g of1-(4-bromophenyl)naphthalene, 0.31 g of Pd₂(dba)₃, 0.52 g oftri-tert-butylphosphine and 1.09 g of NaOtBu were added to a 200 mL,three necked flask, followed by heating, refluxing and stirring in 60 mLof a mixture solvent of toluene for about 6 hours. After air cooling,water was added, an organic layer was separated, and the solvents weredistilled. The crude product thus obtained was separated by silica gelcolumn chromatography (utilizing a mixture solvent of dichloromethaneand hexane) and recrystallized utilizing a mixture solvent of tolueneand ethanol to produce 4.025 g of Compound 213 as a yellow solid (Yield74%).

The molecular weight of Compound 213 measured by FAB-MS was 766. Thechemical shift values (δ) of Compound 213 measured by ¹H-NMR (CDCl₃)were 8.31 (s, 1H), 8.16 (d, 1H, J=6.10 Hz), 7.99 (d, 1H, J=7.00 Hz),7.96 (d, 1H, J=7.20 Hz), 7.96-7.88 (m, 3H), 7.87-7.82 (m, 2H), 7.73 (d,1H, J=7.10 Hz), 7.67-7.53 (m, 10H), 7.51-7.42 (m, 9H), 7.37-7.25 (m,10H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 169

In the synthesis of Compound D in the synthetic method of Compound 17explained above, Compound A was utilized instead of Compound C toprepare an intermediate, and Compound 169 was synthesized utilizing theintermediate by conducting substantially the same procedure describedfor the preparation of Compound 17. The molecular weight of Compound 169measured by FAB-MS was 640. The chemical shift values (δ) of Compound169 measured by ¹H-NMR (CDCl₃) were 8.01-7.89 (m, 6H), 7.68-7.61 (m,6H), 7.56-7.41 (m, 12H), 7.39-7.27 (m, 9H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 181

Compound 181 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 169 except for utilizingN,N-bis([1,1′-biphenyl]-4-yl)-4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-4-amineinstead of Compound A. The molecular weight of Compound 181 measured byFAB-MS was 716. The chemical shift values (δ) of Compound 181 measuredby ¹H-NMR (CDCl₃) were 8.03-7.85 (m, 6H), 7.71-7.67 (m, 8H), 7.53-7.40(m, 14H), 7.37-7.29 (m, 9H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 216

Compound 216 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizing1-iodonaphthalene instead of 1-(4-bromophenyl)naphthalene. The molecularweight of Compound 216 measured by FAB-MS was 690. The chemical shiftvalues (δ) of Compound 216 measured by ¹H-NMR (CDCl₃) were 8.27 (s, 1H),8.03 (d, 1H, J=7.10 Hz), 7.99-7.88 (m, 3H), 7.86-7.78 (m, 4H), 7.72 (d,1H, J=6.80 Hz), 7.62 (d, 1H, J=6.80 Hz), 7.58-7.38 (m, 16H), 7.32-7.22(m, 3H), 7.20-7.09 (m, 5H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 13

(Synthesis of Compound H in Formula 22)

First, the following Compound H was synthesized. Under an Ar atmosphere,29.0 g of Compound E, 13.4 g of 4-chlorophenylboronic acid, 3.14 g ofPd(PPh₃)₄, 38.8 g of K₂CO₃ were added to a 1,000 mL, three necked flask,followed by heating and stirring in a mixture solvent of 300 mL oftoluene and 60 mL of water at about 80° C. for about 4 hours (or about 8hours). After air cooling, water was added, an organic layer wasseparated, and the solvents were distilled. The crude product thusobtained was separated by silica gel column chromatography (utilizing amixture solvent of dichloromethane and hexane) and recrystallizedutilizing a mixture solvent of toluene and acetonitrile to produce 28.2g of Compound H as a white solid (Yield 90%). The molecular weight ofCompound H measured by FAB-MS was 430.

(Synthesis of Compound 13)

Compound 13 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound H instead of 1-(4-bromophenyl)naphthalene and utilizingN-phenyl-1-naphthylamine instead of Compound G. The molecular weight ofCompound 13 measured by FAB-MS was 614. The chemical shift values (δ) ofCompound 13 measured by ¹H-NMR (CDCl₃) were 8.27-8.26 (2H, m), 8.02-7.89(6H, m), 7.83-7.78 (2H, m), 7.72 (2H, d, J=6.0 Hz), 7.63 (2H, d, J=6.6Hz), 7.56-7.39 (11H, m), 7.27-7.21 (3H, m), 7.14-7.09 (3H, m) 7.06 (2H,d, J=7.8 Hz), 6.97 (1H, d, J=6.0 Hz).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 23

Compound 23 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizing2-bromonaphthalene instead of 1-(4-bromophenyl)naphthalene. Themolecular weight of Compound 23 measured by FAB-MS was 690. The chemicalshift values (δ) of Compound 23 measured by ¹H-NMR (CDCl₃) were 8.25 (s,1H), 8.00 (d, 1H, J=7.10 Hz), 7.99-7.88 (m, 3H), 7.82-7.75 (m, 4H), 7.73(d, 1H, J=6.90 Hz), 7.62 (d, 1H, J=6.80 Hz), 7.60-7.48 (m, 16H),7.32-7.22 (m, 3H), 7.18-7.11 (m, 5H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 170 (Synthesis ofN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine)

First, the followingN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine was synthesized.Under an Ar atmosphere, 4.22 g of 4-bromobiphenyl, 4.05 g of1-(4-aminophenyl)naphthalene, 0.78 g of (DPPF)PdCl₂, 1.60 g of DPPF and1.77 g of NaOtBu were added to a 300 mL, three necked flask, followed byheating, refluxing and stirring in 120 mL of a mixture solvent of THFfor about 3 hours. After air cooling, water was added, an organic layerwas separated, and the solvents were distilled. The crude product thusobtained was separated by silica gel column chromatography (utilizing amixture solvent of dichloromethane and hexane) and recrystallizedutilizing a mixture solvent of toluene and ethanol to produce 6.31 g ofa target product as a yellow solid (Yield 92%).

(Synthesis of Compound 170 in Formula 24)

Under an Ar atmosphere, 3.59 g of Compound 1, 2.71 g ofN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine, 0.30 g ofPd₂(dba)₃, 0.54 g of tri-tert-butylphosphine and 2.18 g of NaOtBu wereadded to a 200 mL, three necked flask, followed by heating, refluxingand stirring in 65 mL of a mixture solvent of toluene for about 4 hours(or about 6 hours). After air cooling, water was added, an organic layerwas separated, and the solvents were distilled. The crude product thusobtained was separated by silica gel column chromatography (utilizing amixture solvent of dichloromethane and hexane) and recrystallizedutilizing a mixture solvent of toluene and ethanol to produce 4.19 g ofCompound 170 as a yellow solid (Yield 81%). The molecular weight ofCompound 170 measured by FAB-MS was 689. The chemical shift values (δ)of Compound 170 measured by ¹H-NMR (CDCl₃) were 8.01-7.92 (m, 7H),7.69-7.42 (m, 20H), 7.38-7.33 (m, 8H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 217

Compound 217 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizing1-iodonaphthalene instead of 1-(4-bromophenyl)naphthalene and utilizingCompound F instead of Compound G. The molecular weight of Compound 217measured by FAB-MS was 664. The chemical shift values (δ) of Compound217 measured by ¹H-NMR (CDCl₃) were 8.24 (t, 1H, J=1.2 Hz), 8.11 (d, 2H,J=8.6 Hz), 7.98-7.84 (m, 6H), 7.78-7.69 (m, 4H), 7.63-7.31 (m, 15H),7.20 (t, 2H, J=7.5 Hz), 6.98 (t, 1H, J=7.4 Hz), 6.72 (d, 2H, J=8.7 Hz).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 218 (Synthesis ofN-[4-(1-naphthalenyl)phenyl]-phenyl-4-amine)

First, the following N-[4-(1-naphthalenyl)phenyl]-phenyl-4-amine wassynthesized. Substantially the same procedure described for synthesizingN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphneyl]-4-amine was conductedexcept for utilizing dibromobenzene instead of 4-bromobiphenyl. Themolecular weight measured by FAB-MS was 295.

(Synthesis of Compound 218)

Compound 218 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound H instead of 1-(4-bromophenyl)naphthalene and utilizingN-[4-(1-naphthalenyl)phenyl]-phenyl-4-amine instead of Compound G. Themolecular weight of Compound 218 measured by FAB-MS was 690. Thechemical shift values (δ) of Compound 218 measured by ¹H-NMR (CDCl₃)were 8.31 (S, 1H), 8.08-8.02 (m, 1H), 7.99-7.78 (m, 7H), 7.72 (d, 1H,J=7.5 Hz), 7.64-7.21 (m, 24H), 7.09 (t, 1H, J=7.2).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 220 (Synthesis of4-(1-naphthalenyl)-N-[4-(1-naphthalenyl)phenyl]-benzenamine)

First, the following4-(1-naphthalenyl)-N-[4-(1-naphthalenyl)phenyl-benzenamine wassynthesized. Substantially the same procedure described for synthesizingN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphneyl]-4-amine was conductedexcept for utilizing 1-(4-bromophenyl)naphthalene instead of4-bromobiphenyl. The molecular weight measured by FAB-MS was 421.

(Synthesis of Compound 220)

Compound 220 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound H instead of 1-(4-bromophenyl)naphthalene and utilizing4-(1-naphthalenyl)-N-[4-(1-naphthalenyl)phenyl]-benzenamine instead ofCompound G. The molecular weight of Compound 220 measured by FAB-MS was816. The chemical shift values (δ) of Compound 220 measured by ¹H-NMR(CDCl₃) were 8.78 (d, J=7.8 Hz, 2H), 8.70 (d, J=7.8 Hz, 2H), 8.29 (d,J=8.1 Hz, 2H), 8.24 (t, J=1.5 Hz, 1H), 7.95 (d, J=7.8 Hz, 2H), 7.84 (d,J=7.8 Hz, 2H), 7.79 (d, J=8.0 Hz, 1H), 7.73-7.38 (m, 20H), 7.18 (t,J=7.5 Hz, 2H), 6.98 (t, J=7.5 Hz, 1H), 6.89 (d, J=7.8 Hz, 2H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 222 Synthesis ofN-9-phenanthrenyl-9-phenanthrenamine

First, the following N-9-phenanthrenyl-9-phenanthrenamine wassynthesized. Substantially the same procedure described for synthesizingN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphneyl]-4-amine was conductedexcept for utilizing 9-bromophenanthrene instead of 4-bromobiphenyl andutilizing 9-aminophenanthrene instead of 1-(4-aminophenyl)naphthalene.The molecular weight measured by FAB-MS was 369.

(Synthesis of Compound 222)

Compound 222 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound H instead of 1-(4-bromophenyl)naphthalene and utilizingN-9-phenanthrenyl-9-phenanthrenamine instead of Compound G. Themolecular weight of Compound 222 measured by FAB-MS was 764. Thechemical shift values (δ) of Compound 222 measured by ¹H-NMR (CDCl₃)were 8.78 (d, J=7.8 Hz, 2H), 8.70 (d, J=7.8 Hz, 2H), 8.29 (d, J=8.1 Hz,2H), 8.24 (t, J=1.5 Hz, 1H), 7.95 (d, J=7.8 Hz, 2H), 7.84 (d, J=7.8 Hz,2H), 7.79 (d, J=8.0 Hz, 1H), 7.73-7.38 (m, 20H), 7.18 (t, J=7.5 Hz, H),6.98 (t, J=7.5 Hz, 1H), 6.89 (d, J=7.8 Hz, 2H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 225 (Synthesis ofN-[4-(1-naphthalenyl)phenyl]-1-naphthalenamine)

First, the following N-[4-(1-naphthalenyl)phenyl]-1-naphthalenamine wassynthesized. Substantially the same procedure described for synthesizingN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphneyl]-4-amine was conductedexcept for utilizing 1-iodonaphthalene instead of 4-bromobiphenyl. Themolecular weight measured by FAB-MS was 345.

(Synthesis of Compound 225)

Compound 225 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound E instead of 1-(4-bromophenyl)naphthalene and utilizingN-[4-(1-naphthalenyl)phenyl]-1-naphthalenamine instead of Compound G.The molecular weight of Compound 225 measured by FAB-MS was 664. Thechemical shift values (δ) of Compound 225 measured by ¹H-NMR (CDCl₃)were 8.08 (d, 1H, J=8.1 Hz), 7.98-7.84 (m, 7H), 7.83-7.75 (m, 3H), 7.64(d, 1H, J=7.5 Hz), 7.56 (d, 1H, J=7.8 Hz), 7.54-7.43 (m, 8H), 7.43-7.33(m, 6H), 7.25 (m, 3H), 7.16 (d, 2H, J=8.4 Hz), 7.12 (m, 1H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 226

Compound 226 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound E instead of 1-(4-bromophenyl)naphthalene and utilizing4-(1-naphthalenyl)-N-[4-(1-naphthalenyl)phenyl]-benzenamine instead ofCompound G. The molecular weight of Compound 226 measured by FAB-MS was740. The chemical shift values (δ) of Compound 226 measured by ¹H-NMR(CDCl₃) were 8.02 (d, 2H, J=8.4), 7.96-7.81 (m, 9H), 7.69-7.56 (m, 3H),7.54-7.30 (m, 23H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 229

Compound 229 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound I instead of 1-(4-bromophenyl)naphthalene and utilizing1,1′-dinaphthylamine instead of Compound G. The molecular weight ofCompound 229 measured by FAB-MS was 588. The chemical shift values (δ)of Compound 229 measured by ¹H-NMR (CDCl₃) were 8.12 (d, 2H, J=8.70 Hz),7.95-7.86 (m, 6H), 7.77-7.73 (m, 4H), 7.65 (dd, 1H, J=1.20, 7.60 Hz),7.58 (dd, 1H, J=1.20, 7.60 Hz), 7.52-7.47 (m, 2H), 7.46-7.28 (m, 11H),6.81 (d, 1H, J=9.00 Hz).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 231

Compound 231 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound I instead of 1-(4-bromophenyl)naphthalene and utilizingN-[4-(1-naphthalenyl)phenyl]-1-naphthalenamine instead of Compound G.The molecular weight of Compound 231 measured by FAB-MS was 664. Thechemical shift values (δ) of Compound 231 measured by ¹H-NMR (CDCl₃)were 8.09 (d, J=8.0 Hz, 1H), 8.05 (d, J=8.1 Hz, 1H), 8.00-7.81 (m, 10H),7.66 (d, J=7.8 Hz, 1H), 7.62 (d, J=7.8 Hz, 1H), 7.60-7.33 (m, 15H),7.29-7.2 (m, 4H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 232

Compound 232 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound I instead of 1-(4-bromophenyl)naphthalene and utilizing4-(1-naphthalenyl)phenyl]-N-[4-(1-naphthalenyl)phenyl]-benzenamineinstead of Compound G. The molecular weight of Compound 232 measured byFAB-MS was 740. The chemical shift values (δ) of Compound 232 measuredby ¹H-NMR (CDCl₃) were 8.10 (m, 2H), 7.95-8.05 (m, 7H), 7.87 (d, 2H,J=7.90 Hz), 7.70 (dd, 1H, J1=1, 20 Hz, J2=3, 70 Hz), 7.67 (dd, 1H, J1=1,20 Hz, J2=3, 70 Hz), 7.58-7.34 (m, 21H), 7.24-7.28 (m, 2H), 7.17 (d, 1H,J=7.10 Hz).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 243

Compound 243 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizing1-(3-bromophenyl)naphthalene instead of 1-(4-bromophenyl)naphthalene.The molecular weight of Compound 243 measured by FAB-MS was 766. Thechemical shift values (6) of Compound 243 measured by ¹H-NMR (CDCl₃)were 8.29 (t, 1H, J=1.2 Hz), 8.01-7.81 (m, 8H), 7.73 (dd, 1H, J=7.62Hz), 7.66-7.40 (m, 18H), 7.35-7.28 (m, 8H), 7.22-7.16 (m, 3H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 244 Synthesis ofN-[1,1′-biphenyl]-4-yl-9-phenanthrenamine

First, the following N-[1,1′-biphenyl]-4-yl-9-phenanthrenamine wassynthesized. Substantially the same procedure described for synthesizingN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine was conductedexcept for utilizing 9-aminophenanthrene instead of1-(4-aminophenyl)naphthalene. The molecular weight measured by FAB-MSwas 345.

(Synthesis of Compound 244)

Compound 244 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound H instead of 1-(4-bromophenyl)naphthalene and utilizingN-[1,1′-biphenyl]-4-yl-9-phenanthrenamine instead of Compound G. Themolecular weight of Compound 244 measured by FAB-MS was 740. Thechemical shift values (δ) of Compound 244 measured by ¹H-NMR (CDCl₃)were 8.78 (d, J=8.0 Hz, 1H), 8.74 (d, J=8.0 Hz, 1H), 8.28 (t, J=1.2 Hz,1H), 8.13 (d, J=8.0 Hz, 1H), 7.97 (d, J=8.0 Hz, 2H), 7.87 (d, J=8.1 Hz,2H), 7.81 (d, J=8.1 Hz, 2H), 7.75-7.36 (m, 19H), 7.34-7.16 (m, 6H), 7.11(t, J=7.5 Hz, 2H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 245 Synthesis ofN-[1,1′-biphenyl]-4-yl-2-phenanthrenamine

First, the following N-[1,1′-biphenyl]-4-yl-2-phenanthrenamine wassynthesized. Substantially the same procedure described for synthesizingN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine was conductedexcept for utilizing 2-aminophenanthrene instead of1-(4-aminophenyl)naphthalene. The molecular weight measured by FAB-MSwas 345.

(Synthesis of Compound 245)

Compound 245 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound E instead of 1-(4-bromophenyl)naphthalene and utilizingN-[1,1′-biphenyl]-4-yl-2-phenanthrenamine instead of Compound G. Themolecular weight of Compound 245 measured by FAB-MS was 664. Thechemical shift values (δ) of Compound 245 measured by ¹H-NMR (CDCl₃)were 8.56 (d, J=7.8 Hz, 1H), 8.52 (d, J=8.0 Hz, 1H), 8.00-7.91 (m, 4H),7.83 (d, J=8.0 Hz, 1H), 7.77 (t, J=1.5 Hz, 1H), 7.71-7.24 (m, 25H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 246

(Synthesis of Compound M in Formula 31)

First, the following Compound M was synthesized. Under an Ar atmosphere,29.0 g of Compound E, 13.4 g of 3-chlorophenylboronic acid, 3.14 g ofPd(PPh₃)₄, and 38.8 g of K₂CO₃ were added to a 1,000 mL, three neckedflask, followed by heating and stirring in a mixture solvent of 300 mLof toluene and 60 ml of water at about 80° C. for about 4 hours (orabout 8 hours). After air cooling, water was added, an organic layer wasseparated, and the solvents were distilled. The crude product thusobtained was separated utilizing silica gel column chromatography(utilizing a mixture solvent of dichloromethane and hexane) andrecrystallized utilizing a mixture solvent of toluene and acetonitrileto produce 28.2 g of Compound M as a white solid (Yield 90%). Themolecular weight of Compound M measured by FAB-MS was 430.

(Synthesis of Compound 246)

Compound 246 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound M instead of 1-(4-bromophenyl)naphthalene and utilizingN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine instead of CompoundG. The molecular weight of Compound 246 measured by FAB-MS was 766. Thechemical shift values (δ) of Compound 246 measured by ¹H-NMR (CDCl₃)were 8.28 (s, 1H), 8.05-7.80 (m, 8H), 7.70 (t, 2H, J=8.2 Hz), 7.62-7.25(m, 28H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 251 in Formula 32

Under an Ar atmosphere, 4.79 g of Compound E, 3.71 g ofN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine, 0.40 g ofPd₂(dba)₃, 0.72 g of tri-tert-butylphosphine and 2.90 g of NaOtBu wereadded to a 200 mL, three necked flask, followed by heating and stirringin 87 mL of a mixture solvent of toluene for about 5 hours (or about 6hours). After air cooling, water was added, an organic layer wasseparated, and the solvents were distilled. The crude product thusobtained was separated utilizing silica gel column chromatography(utilizing a mixture solvent of dichloromethane and hexane) andrecrystallized utilizing a mixture solvent of toluene and ethanol toproduce 5.50 g of Compound 251 as a white solid (Yield 80%). Themolecular weight of Compound 251 measured by FAB-MS was 689. Thechemical shift values (δ) of Compound 251 measured by ¹H-NMR (CDCl₃)were 8.00 (d, J=8.4 Hz, 1H), 7.98-7.93 (m, 4H), 7.89 (d, J=8.1 Hz, 1H),7.83 (d, J=8.4 Hz, 1H), 7.79 (t, J=2.1 Hz, 1H), 7.68-7.65 (m, 2H),7.62-7.53 (m, 3H), 7.52-7.26 (m, 22H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 235

(Synthesis of Compound J in Formula 33)

First, the following Compound J was synthesized. Under an Ar atmosphere,27.6 g of Compound E, 12.4 g of 4-chlorophenylboronic acid, 3.10 g ofPd(PPh₃)₄, and 37.8 g of K₂CO₃ were added to a 1,000 mL, three neckedflask, followed by heating and stirring in a mixture solvent of 300 mLof toluene and 60 ml of water at about 80° C. for about 4 hours (orabout 8 hours). After air cooling, water was added, an organic layer wasseparated, and the solvents were distilled. The crude product thusobtained was separated utilizing silica gel column chromatography(utilizing a mixture solvent of dichloromethane and hexane) andrecrystallized utilizing a mixture solvent of toluene and acetonitrileto produce 26.8 g of Compound J as a white solid (Yield 90%). Themolecular weight of Compound J measured by FAB-MS was 430.

(Synthesis of Compound 235)

Compound 235 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound J instead of 1-(4-bromophenyl)naphthalene and utilizing1,1′-dinaphthylamine instead of Compound G. The molecular weight ofCompound 235 measured by FAB-MS was 664. The chemical shift values (δ)of Compound 235 measured by ¹H-NMR (CDCl₃) were 8.22-8.15 (4H, m), 8.07(2H, d, J=7.80 Hz), 8.03-7.90 (4H, m), 7.81-7.69 (8H, m), 7.50-7.35 (9H,m), 7.37-7.28 (6H, m).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 242

(Synthesis of Compound K in Formula 34)

Under an Ar atmosphere, 8.51 g of 4-phenylphenol, 10.0 g of3-bromo-2-fluoro-benzonitrile, and 13.8 g of potassium carbonate wereadded to a 200 mL, three necked flask, followed by heating and refluxingin 72 mL of a mixture solvent of DMF for about 3 hours (or about 4hours). After air cooling, water and ethyl acetate were added, anorganic layer was separated, and the solvents were distilled. To thecrude product thus obtained, 20.0 g of sodium hydroxide, 140 mL ofdioxane, 140 mL of ethanol and 60 mL of water were added, followed byheating and refluxing for about 20 hours (or about 24 hours). The crudeproduct thus obtained was separated utilizing silica gel columnchromatography (utilizing a mixture solvent of dichloromethane andmethanol) and recrystallized utilizing a mixture solvent of toluene andethanol to produce 14.2 g of a target product (Compound K) as a yellowsolid (Yield 77%).

(Synthesis of Compound L in Formula 35)

Under an Ar atmosphere, 6.80 g of Compound K, 0.343 g of Rh(acac)(cod),and 1.53 g of potassium iodide were added to a 30 mL, two necked flask,followed by heating and stirring in 5.22 mL of a Ac₂O solvent at about160° C. for about 10 hours. After air cooling, water and chloroform wereadded, an organic layer was separated, and the solvents were distilled.The crude product thus obtained was separated utilizing silica gelcolumn chromatography (utilizing a mixture solvent of dichloromethaneand hexane) and recrystallized utilizing a mixture solvent of tolueneand hexane to produce 1.19 g of a target product (Compound L) as ayellow solid (Yield 20%).

(Synthesis of Compound 242 in Formula 36)

The following Compound 242 was synthesized. Under an Ar atmosphere, 1.51g of Compound A, 0.85 g of Compound L, 1.54 g of Pd(PPh₃)₄, and 1.65 gof K₂CO₃ were added to a 300 mL, three necked flask, followed by heatingand stirring in a mixture solvent of 20 mL of toluene and 5 ml of waterat about 90° C. for about 8 hours. After air cooling, water was added,an organic layer was separated, and the solvents were distilled. Thecrude product thus obtained was separated utilizing silica gel columnchromatography (utilizing a mixture solvent of dichloromethane andhexane) and recrystallized utilizing a mixture solvent of toluene andhexane to produce 1.48 g of Compound 242 as a white solid (Yield 88%).The molecular weight of Compound 242 measured by FAB-MS was 640. Thechemical shift values (δ) of Compound 242 measured by ¹H-NMR (CDCl₃)were 8.15 (d, 1H, J=1.20 Hz), 8.01 (d, 1H, J=8.10 Hz), 7.79 (d, 1H,J=0.90 Hz), 7.71-7.68 (m, 3H), 7.65-7.51 (m, 13H), 7.47 (d, 1H, J=7.80Hz), 7.43-7.21 (m, 13H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 248

(Synthesis of Compound N in Formula 37)

The following Compound N was synthesized. Under an Ar atmosphere, 1.02 gof biphenylboronic acid, 3.70 g of 4,6-dibromodibenzofuran, 0.24 g ofPd(PPh₃)₄, and 1.00 g of potassium carbonate were added to a 300 mL,three necked flask, followed by heating and stirring in a mixturesolvent of 50 mL of toluene and 20 mL of water at about 90° C. for about8 hours. After air cooling, water was added, an organic layer wasseparated, and the solvents were distilled. The crude product thusobtained was separated utilizing silica gel column chromatography(utilizing a mixture solvent of dichloromethane and hexane) andrecrystallized utilizing a mixture solvent of toluene and hexane toproduce 1.08 g of Compound N as a white solid (Yield 54%). The molecularweight of Compound N measured by FAB-MS was 399.

(Synthesis of Compound 248)

Compound 248 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound D except for utilizingCompound N instead of 4,6-dibromodibenzofuran and utilizing Compound Ainstead of Compound C. The molecular weight of Compound 248 measured byFAB-MS was 716. The chemical shift values (δ) of Compound 248 measuredby ¹H-NMR (CDCl₃) were 8.09 (d, 2H, J=8.40 Hz), 8.01-7.89 (m, 4H),7.74-7.72 (m, 3H), 7.68-7.42 (m, 17H), 7.37-7.21 (m, 11H). From theresults, the synthesized white solid was determined as Compound 248.

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 253 (Synthesis ofN-[4-(2-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine)

First, the followingN-[4-(2-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine was synthesized.Substantially the same procedure described for synthesizingN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine was conductedexcept for utilizing 2-(4-aminophenyl)naphthalene instead of1-(4-aminophenyl)naphthalene. The molecular weight measured by FAB-MSwas 371.

(Synthesis of Compound 253)

Compound 253 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound H instead of 1-(4-bromophenyl)naphthalene and utilizingN-[4-(2-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine instead of CompoundG. The molecular weight of Compound 253 measured by FAB-MS was 766. Thechemical shift values (δ) of Compound 253 measured by ¹H-NMR (CDCl₃)were 8.32 (t, J=1.5 Hz, 1H), 8.05 (s, 1H), 8.02-7.97 (m, 2H), 7.96-7.82(m, 6H), 7.78-7.73 (m, 2H), 7.72-7.53 (m, 11H), 7.52-7.41 (m, 6H),7.37-7.24 (m, 10H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 254 Synthesis ofN-2-dibenzofuranyl-2-dibenzofuranamine

The following N-2-dibenzofuranyl-2-dibenzofuranamine was synthesized.Substantially the same procedure described for synthesizingN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine was conductedexcept for utilizing 3-bromodibenzofuran instead of 4-bromobiphenyl andutilizing 3-aminodibenzofuran instead of 1-(4-aminophenyl)naphthalene.The molecular weight measured by FAB-MS was 349.

(Synthesis of Compound 254)

Compound 254 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound H instead of 1-(4-bromophenyl)naphthalene and utilizingN-2-dibenzofuranyl-2-dibenzofuranamine instead of Compound G. Themolecular weight of Compound 254 measured by FAB-MS was 668. Thechemical shift values (δ) of Compound 254 measured by ¹H-NMR (CDCl₃)were 7.99-7.95 (m, 8H), 7.83 (d, 2H, J=8.4 Hz), 7.66 (d, 2H, J=7.8 Hz),7.54-7.29 (m, 15H), 7.23 (d, 2H, J=8.4 Hz).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 256 Synthesis ofN-[1,1′-biphenyl]-4-yl-1-naphthalenamine

The following N-[1,1′-biphenyl]-4-yl-1-naphthalenamine was synthesized.Substantially the same procedure described for synthesizingN-[4-(1-naphthalenyl)phenyl]-[1,1′-biphenyl]-4-amine was conductedexcept for utilizing 1-aminonaphthalene instead of1-(4-aminophenyl)naphthalene. The molecular weight measured by FAB-MSwas 295.

(Synthesis of Compound 256)

Compound 256 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound I instead of 1-(4-bromophenyl)naphthalene and utilizingN-[1,1′-biphenyl]-4-yl-1-naphthaleneamine instead of Compound G. Themolecular weight of Compound 256 measured by FAB-MS was 614. Thechemical shift values (δ) of Compound 256 measured by ¹H-NMR (CDCl₃)were 8.02 (d, 1H, J=8.50 Hz), 7.90-7.88 (m, 5H), 7.84-7.80 (m, 3H),7.68-7.37 (m, 17H), 7.29 (dt, 1H, J=9.10, 2.30 Hz), 7.23-7.15 (m, 4H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 257

Compound 257 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound E instead of 1-(4-bromophenyl)naphthalene and utilizingN-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine instead of Compound G.The molecular weight of Compound 257 measured by FAB-MS was 640. Thechemical shift values (δ) of Compound 257 measured by ¹H-NMR (CDCl₃)were 7.95 (m, 4H), 7.74 (m, 1H), 7.66 (m, 1H), 7.64 (m, 1H), 7.58 (m,2H), 7.55 (m, 3H), 7.54-7.15 (m, 21H).

In addition, the material for an organic EL device according to anembodiment may be synthesized, for example, as follows.

Synthesis of Compound 258

Compound 258 was synthesized by conducting substantially the sameprocedure described for synthesizing Compound 213 except for utilizingCompound E instead of 1-(4-bromophenyl)naphthalene and utilizingN-[1,1′-biphenyl]-4-yl-1-naphthalenamine instead of Compound G. Themolecular weight of Compound 258 measured by FAB-MS was 614. Thechemical shift values (δ) of Compound 258 measured by ¹H-NMR (CDCl₃)were 8.01 (d, 1H, J=8.44 Hz), 7.99-7.90 (m, 4H), 7.88 (d, 1H, J=8.44Hz), 7.77 (d, 1H, J=7.92 Hz), 7.71 (t, 1H, J=1.98 Hz), 7.64 (dd, 1H,J=1.23, 7.61 Hz), 7.57-7.22 (m, 19H), 7.11 (dt, 2H, J=9.14, 2.39 Hz),7.04 (ddd, 1H, J=8.13, 2.31, 1.00 Hz).

Examples

Organic EL devices according to Examples 1 to 9 were manufacturedutilizing the hole transport materials of Compound 5, Compound 17,Compound 77, Compound 89, Compound 141, Compound 169, Compound 181,Compound 213 and Compound 216 by the above-described manufacturingmethod.

As Comparative Examples, organic EL devices according to ComparativeExamples 1 to 5 were manufactured utilizing hole transport materials ofComparative Compounds C1 to C5.

An organic EL device 300 according to Examples 1 to 9 is shown in FIG.3. In Examples 1 to 9, a transparent glass substrate was utilized as asubstrate 302, an anode 304 was formed utilizing ITO to a layerthickness of about 150 nm, a hole injection layer 306 was formedutilizing 2-TNATA to a layer thickness of about 60 nm, a hole transportlayer 308 was formed to a layer thickness of about 30 nm, an emissionlayer 310 was formed utilizing ADN doped with 3% TBP to a layerthickness of about 25 nm, an electron transport layer 312 was formedutilizing Alq3 to a layer thickness of about 25 nm, an electroninjection layer 314 was formed utilizing LiF to a layer thickness ofabout 1 nm, and a cathode 316 was formed utilizing Al to a layerthickness of about 100 nm.

For the organic EL devices 300, driving voltages and half life wereevaluated. The voltage and emission efficiency were obtained at currentdensity of about 10 mA/cm², and the half life was a time period fordecreasing the value of luminance to half from an initial luminance ofabout 1,000 cd/m². Evaluation results are shown in Table 1.

TABLE 1 Device Emission manufacturing Hole transport Voltage efficiencyLife LT50 example layer (V) (cd/A) (h) Example 1 Compound 5 5.6 6.72,200 Example 2 Compound 17 5.6 6.7 2,250 Example 3 Compound 77 5.4 6.82,000 Example 4 Compound 89 5.3 6.8 2,050 Example 5 Compound 141 5.5 6.52,000 Example 6 Compound 169 5.5 6.7 2,200 Example 7 Compound 181 5.56.7 2,150 Example 8 Compound 213 5.5 6.7 2,150 Example 9 Compound 2165.5 6.7 2,100 Comparative Comparative 6.3 5.2 1,600 Example 1 CompoundC1 Comparative Comparative 6.5 5.0 1,450 Example 2 Compound C2Comparative Comparative 6.6 5.2 1,500 Example 3 Compound C3 ComparativeComparative 6.6 5.1 1,600 Example 4 Compound C4 Comparative Comparative6.6 5.3 1,600 Example 5 Compound C5

Referring to Table 1, the organic EL devices according to Examples 1 to9 had longer life and improved emission efficiency when compared tothose according to Comparative Examples 1 to 5. In Examples 1 to 9, asubstituted dibenzoheterole group with high electron tolerance wasintroduced in an amine group, and so, the electron tolerance of the holetransport layer was improved, and the life thereof was increased. InExamples 1 to 4, molecular symmetry was broken, amorphous propertieswere improved, and high device efficiency was obtained by substitutingan m-phenylene group in the amine group with the substituteddibenzoheterole group. In Examples 5 to 9, molecular symmetry wasbroken, amorphous properties were improved, and high device efficiencywas obtained by substituting a p-phenylene group in the amine group withthe substituted dibenzoheterole group. If an unsubstituteddibenzoheterole group was present as in Comparative Examples 1, 3, 4 and5, a group with high electron density in the dibenzoheterole was notsubstituted with a substituent, and it would be suggested that amaterial was easily deteriorated, and the life of a device wasdecreased. In Comparative Examples 1, 3 and 5, Comparative Compounds C1,C3 and C5 did not include a substituent in the dibenzofuran and hadinsufficient amorphous properties when compared to that of Examples 1 to9, thereby having short device life and low emission efficiency. InComparative Example 2, a carbazole group was included, and the electronaccepting properties of a hole transport layer was increased, electronsremained in the hole transport layer, and device life was deteriorated.

From the results of Table 1, long life and high efficiency wererecognized if the material for an organic EL device according to anembodiment was utilized as the hole transport material in considerationof the compounds of the comparative examples. Since the material for anorganic EL device according to an embodiment included the substituteddibenzoheterole group in an amine compound, the amine compound showinghole transport properties, the electron tolerance and amorphousproperties of the material were improved, and high emission efficiencyand long life were realized.

In addition, organic EL devices according to Examples 10 to 43 weremanufactured utilizing Compound 5, Compound 13, Compound 17, Compound23, Compound 77, Compound 89, Compound 141, Compound 169, Compound 170,Compound 181, Compound 213, Compound 216, Compound 217, Compound 218,Compound 220, Compound 222, Compound 225, Compound 226, Compound 229,Compound 231, Compound 232, Compound 235, Compound 242, Compound 243,Compound 244, Compound 245, Compound 246, Compound 248, Compound 251,Compound 253, Compound 254, Compound 256, Compound 257 and Compound 258as the hole transport materials and by the above-described manufacturingmethod.

FIG. 4 is a schematic diagram illustrating an organic EL device 400according to Examples 10 to 43. In Examples 10 to 43, an anode 404 wasformed utilizing ITO to a layer thickness of about 150 nm. On the anode404, HTL1 was formed as a hole injection layer 408 by doping thefollowing Compound 286 shown by Structure ac14 as an electron acceptingcompound to a layer thickness of about 10 nm. On the hole injectionlayer 408, HTL2 was formed utilizing Compound 272 to a layer thicknessof about 10 nm as a first hole transport layer 410. On the first holetransport layer 410, HTL3 was formed utilizing the material for anorganic EL device according to an embodiment to a layer thickness ofabout 10 nm as a second hole transport layer 412. Then, an emissionlayer 414 was formed by utilizing Compound a-7 as a host material anddoping 3% of Compound 287 as a luminescent material (doping material) byco-deposition to a layer thickness of about 25 nm. An electron transportlayer 416 was formed utilizing Alq3 to a layer thickness of about 25 nm,an electron injection layer 418 was formed utilizing LiF to a layerthickness of about 1 nm, and a cathode 420 was formed utilizing Al to alayer thickness of about 100 nm.

Organic EL devices according to Comparative Examples 6 to 10 weremanufactured utilizing Comparative Compounds C1 to C5 as hole transportmaterials.

For the organic EL devices 400, driving voltages and half life wereevaluated. The voltage and emission efficiency were obtained at currentdensity of about 10 mA/cm², and the half life was a time period fordecreasing the value of luminance to half from an initial luminance ofabout 1,000 cd/m². Evaluation results are shown in Table 2.

TABLE 2 Device Emission manufacturing Hole transport Voltage efficiencyLife LT50 example layer (V) (cd/A) (h) Example 10 Compound 5 5.6 6.742,000 Example 11 Compound 13 5.5 6.8 1,900 Example 12 Compound 17 5.66.74 2,150 Example 13 Compound 23 5.4 6.7 2,000 Example 14 Compound 775.4 6.7 2,000 Example 15 Compound 89 5.2 6.74 2,000 Example 16 Compound141 5.5 6.7 2.000 Example 17 Compound 169 5.5 6.5 2,050 Example 18Compound 170 5.6 6.6 2,050 Example 19 Compound 181 5.5 6.5 2,050 Example20 Compound 213 5.5 6.7 2,000 Example 21 Compound 216 5.5 6.8 1,950Example 22 Compound 217 5.7 6.9 1,900 Example 23 Compound 218 5.5 6.81,950 Example 24 Compound 220 5.6 6.8 1,950 Example 25 Compound 222 5.76.7 1,900 Example 26 Compound 225 5.5 6.8 1,950 Example 27 Compound 2265.6 6.8 1,950 Example 28 Compound 229 5.6 6.8 2,000 Example 29 Compound231 5.5 6.6 2,000 Example 30 Compound 232 5.6 6.6 2,050 Example 31Compound 235 5.6 6.6 2,050 Example 32 Compound 242 5.6 6.6 2,000 Example33 Compound 243 5.5 6.8 1,950 Example 34 Compound 244 5.6 6.7 1,900Example 35 Compound 245 5.6 6.7 1,950 Example 36 Compound 246 5.7 6.71,950 Example 37 Compound 248 5.6 6.5 2,000 Example 38 Compound 251 5.56.8 2,000 Example 39 Compound 253 5.5 6.7 1,950 Example 40 Compound 2545.6 6.4 2,050 Example 41 Compound 256 5.6 6.6 2,050 Example 42 Compound257 5.6 6.7 1,900 Example 43 Compound 258 5.4 6.8 1,950 ComparativeComparative 6.3 5.2 1,550 Example 6 Compound C1 Comparative Comparative6.5 5.0 1,450 Example 7 Compound C2 Comparative Comparative 6.6 5.21,500 Example 8 Compound C3 Comparative Comparative 6.6 5.1 1,550Example 9 Compound C4 Comparative Comparative 6.6 5.3 1,550 Example 10Compound C5

Referring to the results in Table 2, the organic EL devices according toExamples 10 to 43 showed long life and improved emission efficiency whencompared to those according to Comparative Examples 6 to 10. In Examples10 to 43, the second hole transport layer 412 formed utilizing thematerial for an organic EL device according to an embodiment, in which asubstituted dibenzoheterole group with high electron tolerance wasintroduced into an amine compound, had increased electron tolerance andlong life. By disposing the second hole transport layer 412 adjacent tothe emission layer 414, electrons not consumed in the emission layer 414was not diffused into the hole transport band 406 at the anode 404 sidedue to the second hole transport layer 412, the layers of the holetransport band 406 could be passivated, and long life could be obtained.In the material for an organic EL device according to an embodimentutilizing a compound in which an amine group and an m-phenylene groupare combined, i.e., in Examples 10 to 16, 20 to 27, 33 to 36, 38, 39, 42and 43, relatively higher device efficiency was obtained. In thematerial for an organic EL device according to an embodiment utilizing acompound in which an amine group and a p-phenylene group are combined,i.e., in Examples 17 to 19, 28 to 32, 37, 40 and 41, relatively longerlife was obtained.

If an unsubstituted dibenzoheterole group was present as in ComparativeExamples 6, 8, 9 and 10, the material was easily deteriorated, anddevice life was decreased, because a group with high electron density ofthe dibenzoheterole was not substituted with a substituent.

In Comparative Examples 6, 8 and 10, since Comparative Compounds C1, C3and C5 did not include a substituent in the dibenzofuran, amorphousproperties were insufficient, device life was short, and emissionefficiency was low when compared to Examples 10 to 43. In ComparativeExample 7, the amine compound included a carbazole group, and theelectron accepting properties of the second hole transport layer 412 wasincreased, and electrons remained in the second hole transport layer412, thereby decreasing the device life.

By introducing the substituted dibenzoheterole group into the aminecompound in the material for an organic EL device according to anembodiment, the electron tolerance and amorphous properties of thematerial may be improved. Thus, the high emission efficiency and longlife of an organic EL device may be realized. Since the material for anorganic EL device according to an embodiment has a wide energy gap,application to a red emission region may be possible.

According to an embodiment, a material for an organic EL device havinghigh emission efficiency and long life, and an organic EL deviceincluding the same may be provided. According to an embodiment, amaterial for an organic EL device having high emission efficiency andlong life particularly within a range from a green emission region to ablue emission region, and an organic EL device including the same in atleast one layer of stacking layers disposed between an emission layerand an anode may be provided. Since the material for an organic ELdevice according to an embodiment introduces (e.g., includes) asubstituted dibenzoheterole group with high electron tolerance in anamine compound, a layer utilizing the material for an organic EL deviceaccording to an embodiment and having high efficiency and long life maybe realized. Further, an organic EL device having high efficiency andlong life may be manufactured.

As used herein, the term “substantially,” “about,” and similar terms areused as terms of approximation and not as terms of degree, and areintended to account for the inherent deviations in measured orcalculated values that would be recognized by those of ordinary skill inthe art. Also, any numerical range recited herein is intended to includeall sub-ranges of the same numerical precision subsumed within therecited range. For example, a range of “1.0 to 10.0” is intended toinclude all subranges between (and including) the recited minimum valueof 1.0 and the recited maximum value of 10.0, that is, having a minimumvalue equal to or greater than 1.0 and a maximum value equal to or lessthan 10.0, such as, for example, 2.4 to 7.6. Any maximum numericallimitation recited herein is intended to include all lower numericallimitations subsumed therein and any minimum numerical limitationrecited in this specification is intended to include all highernumerical limitations subsumed therein. Accordingly, Applicant reservesthe right to amend this specification, including the claims, toexpressly recite any sub-range subsumed within the ranges expresslyrecited herein.

Expressions such as “at least one of,” when preceding a list ofelements, modify the entire list of elements and do not modify theindividual elements of the list. Further, the use of “may” whendescribing embodiments of the disclosure refers to “one or moreembodiments of the disclosure.” Also, the term “exemplary” is intendedto refer to an example or illustration.

The above-disclosed subject matter is to be considered illustrative andnot restrictive, and the appended claims are intended to cover all suchmodifications, enhancements, and other embodiments, which fall withinthe true spirit and scope of the disclosure. Thus, to the maximum extentallowed by law, the scope of the disclosure is to be determined by thebroadest permissible interpretation of the following claims and theirequivalents, and shall not be restricted or limited by the foregoingdetailed description.

1. A material for an organic electroluminescent (EL) device representedby Formula 5:

wherein in Formula 5, X₂ is O or S; Ar₅ and Ar₆ are each independently asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms forforming a ring, a silyl group, a halogen atom, a deuterium atom, ahydrogen atom, or a substituted or unsubstituted dibenzoheterole grouphaving 10 to 30 carbon atoms for forming a ring and including an oxygenatom or a sulfur atom; L6 is a direct linkage or a divalent groupselected from a substituted or unsubstituted aryl group having 6 to 24carbon atoms for forming a ring and a silyl group. 2-7. (canceled)
 8. Anorganic electroluminescent (EL) device, comprising the material for anorganic EL device of claim 1 in at least one layer of a plurality ofstacking layers between an emission layer and an anode. 9-13. (canceled)14. An organic EL device of claim 8, wherein the material for theorganic EL device is included in a first layer adjacent to the emissionlayer.
 15. An organic EL device of claim 14, wherein the plurality ofstacking layers comprises a second layer comprising an electronaccepting compound having a lowest unoccupied molecular orbital (LUMO)level within a range from about −9.0 eV to about −4.0 eV, the secondlayer between the anode and the first layer.
 16. An organic EL device ofclaim 15, wherein the plurality of stacking layers comprises a thirdlayer comprising an amine derivative represented by Formula 8, the thirdlayer between the first layer and the second layer:

wherein in Formula 8, Ar₉, Ar₁₀ and Ar₁₁ are each independently asubstituted or unsubstituted aryl group having 6 to 50 carbon atoms forforming a ring, or a substituted or unsubstituted heteroaryl grouphaving 5 to 50 carbon atoms for forming a ring; Ar₁₂ is a substituted orunsubstituted aryl group having 6 to 50 carbon atoms for forming a ring,a substituted or unsubstituted heteroaryl group having 5 to 50 carbonatoms for forming a ring, or a substituted or unsubstituted alkyl grouphaving 1 to 50 carbon atoms; and L₇ is a direct linkage, a substitutedor unsubstituted arylene group having 6 to 18 carbon atoms for forming aring, or a substituted or unsubstituted heteroarylene group having 5 to15 carbon atoms for forming a ring. 17-20. (canceled)